HK1021731B - Thienopyrimidines - Google Patents

Description

Thienopyrimidine compounds

The present invention relates to compounds of formula I:wherein R is¹，R²In each case independently of one another, represents H, A, OA, alkenyl, alkyne

Basic group, NO₂，CF₃Or Hal, wherein R¹Or R²One of them always cannot be hydrogen, R¹And R²And together also represents an alkylene radical having 3 to 5 carbon atoms, R³，R⁴In each case independently of one another, represents H, A, OA, Hal, NO₂，

NH₂NHA or NAA', R³And R⁴Together also represent-O-CH₂CH₂-，-O-CH₂-O-or-O-CH₂-CH₂-O-, A, A' in each case independently of one another represent alkyl having 1 to 6 carbon atoms, X represents a group bonded via N or C having 1 to 4N, O and/or S atoms

Unsaturated 5-7 membered heterocyclic ring, unsubstituted or substituted by A, Hal or CF₃

Mono-, di-or tri-substituted, and the other CH in the heterocyclic ring₂May also be substituted by NH,

NA, S or O, Hal represents F, Cl, Br or I, and n represents 0, 1, 2 or 3.

Pyrimidine derivatives are described, for example, in EP201188 or WO 93/06104.

The object of the present invention was to develop new compounds with important properties, in particular compounds which can be used for the preparation of medicaments.

It has been found that the compounds of formula I and their salts have very important pharmacological properties while also being well tolerated.

In particular, these compounds show specific inhibition of cGMP Phosphodiesterase (PDEV).

Quinazoline compounds having cGMP phosphodiesterase inhibitory activity are described, for example, in journal of medicinal chemistry (j.med. chem.) in 36, 3765(1993) and supra in 37, 2106 (1994).

The biological activity of the compounds of the formula I according to the invention can be determined, for example, by the method described in WO 93/06104.

The affinity of the compounds of the invention for cGMP and cAMP phosphodiesterase is determined by determining their IC₅₀Value (i.e., the concentration of inhibitor required to obtain 50% inhibition of enzyme activity).

For performing these assays, enzymes isolated by conventional methods can be used (e.g., w.j. thompson et al, biochemistry (Biochem.), 1971, 10, 311). Also for these experiments, a modified batch process of w.j.thompson and m.m.appleman (biochemistry 1979, 18, 5228) may be used.

The compounds according to the invention are therefore suitable for the treatment of diseases of the cardiovascular system, in particular cardiac insufficiency, and also for the treatment of impaired sexual intercourse.

The compounds of formula I are useful as pharmaceutically active ingredients in human and veterinary medicine. In addition, they can be used as intermediates for the preparation of other pharmaceutically active ingredients.

To this end, the invention relates to compounds of the formula I and to the preparation thereof as described below: a) for compounds of formula I according to claim 1, wherein X is bonded via N, and salts thereof, the process is characterized by reacting a compound of formula II:wherein R is¹，R²，R³，R⁴And n is as defined above, and L represents Cl, Br, OH, SCH₃Or a reactive esterified OH group with a 5-to 7-membered unsaturated heterocycle having at least one NH group, wherein the unsaturated heterocycle is unsubstituted or substituted by A, Hal or CF₃Mono-, di-or trisubstituted, and in said unsaturated heterocyclesOther CH of₂May also be replaced by NH, NA, S or O,

or b) for compounds of the formula I according to claim 1 in which X is bonded via C and their salts, characterized in that a compound of the formula III:wherein

R¹，R²And X is as defined above, and L is Cl, Br, OH, SCH₃Or a reactive esterified OH group with a compound of formula IV:wherein R is³，R⁴And n is as defined above, and n is,

or c) the process is further characterized in that the radical R in the compounds of the formula I is reacted in the following manner¹，R²，R³And/or R⁴Conversion into different radicals R¹，R²，R³And/or R⁴: i.e. reduction of the nitro group, conversion of a primary or secondary amino group to an alkylated amine by reductive amination, or acylation of such an amino group, and/or which process is characterized in that a basic compound of formula I is converted into a salt by treatment with an acid.

In this context, the radical R¹，R²，R³，R⁴X, L and n have the meanings given in formulae I, II, III, IV and V, unless explicitly stated otherwise.

A and A' are in each case, independently of one another, preferably alkyl having from 1 to 6 carbon atoms.

In each of the above formulae, the alkyl group is preferably in the form of a straight chain and has 1, 2, 3, 4, 5 or 6 carbon atoms, preferably 1, 2, 3, 4 or 5 carbon atoms, and is preferably methyl, ethyl or propyl, furthermore preferably isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, and furthermore preferably n-pentyl, neopentyl or isopentyl.

The alkylene group is preferably in an unbranched form, and is preferably propylene, butylene or pentylene.

Radical R¹And R²Of these, when one is preferably H, the other is preferably propyl or butyl, although ethyl or methyl is particularly preferred. Furthermore, R¹And R²Together also preferably represent propylene, butylene or pentylene.

Hal is preferably F, Cl or Br, and also preferably I.

Alkenyl is preferably vinyl, 1-or 2-propenyl, 1-butenyl, isobutenyl, sec-butenyl, furthermore preferably 1-pentenyl, isopentenyl or 1-hexenyl.

Alkynyl is preferably ethynyl, propyn-1-yl, furthermore butyn-1-yl, butyn-2-yl, pentyn-1-yl, pentyn-2-yl or pentyn-3-yl.

Radical R³And R⁴May be the same or different and is preferably located at the 3-or 4-position of the phenyl ring. For example, they are in each case independently of one another H, alkyl, alkoxy, nitro, amino, alkylamino (for example methylamino), dialkylamino (for example dimethylamino), F, Cl, Br or I or together represent ethylenemonooxy, methylenedioxy or ethylenedioxy. It is also preferred that they represent in each case an alkoxy group, for example a methoxy, ethoxy or propoxy group.

The radical X preferably represents 2-or 3-furyl, 2-or 3-thienyl, 1-, 2-or 3-pyrrolyl, 1-, 2-, 4-or 5-imidazolyl, 2-methyl-1-imidazol-1-yl, 1-, 3-, 4-or 5-pyrazolyl, 2-, 4-or 5-oxazolyl, 3-, 4-, or 5-isoxazolyl, 2-, 4-or 5-thiazolyl, 3-, 4-or 5-isothiazolyl, 2-, 3-or 4-pyridyl, 2-, 4-, 5-or 6-pyrimidinyl, preference being given furthermore to 1, 2, 3-triazol-1-, 1-, 2-, 3-pyrrolyl and 2-, 4-or 5-pyrazolyl, -4-or-5-yl, 1, 2, 4-triazol-1-, -3-or-5-yl, 1-or 5-tetrazolyl, 1, 2, 3-oxadiazol-4-or-5-yl, 1, 2, 4-oxadiazol-3-or-5-yl, 1, 3, 4-thiadiazol-2-or-5-yl, 1, 2, 4-thiadiazol-3-or-5-yl, 1, 2, 3-thiadiazol-4-or-5-yl, 3-or 4-pyridazinyl or pyrazinyl, each of which is unsubstituted or substituted by alkyl Hal, or CF₃Mono-, di-or tri-substituted.

When all of the groups occur more than once, they may be the same or different, i.e., independent of each other, and this rule applies to the entire invention.

The present invention therefore relates in particular to those compounds of the formula I in which at least one of the abovementioned radicals has one of the abovementioned preferred definitions. Some preferred groups of compounds can be represented by the following subformulae Ia to Ie, which correspond to the compounds of formula I, wherein the definitions of the various radicals which are not described in detail are as described for formula I, except for the following radical definitions: in Ia, X represents imidazolyl or pyridyl; in Ib, R¹，R²In each case independently of one another, represents H, A, OA,

NO₂，CF₃or Hal, where the radical R¹Or R²At least one of which is not always H,

R³and R⁴Together represent-O-CH₂-CH₂-，-O-CH₂-O-or-O-CH₂-CH₂-O，

X represents imidazolyl or pyridyl, and

n represents 1; in Ic, R¹，R²In each case independently of one another, represents H, A, OA,

NO₂，CF₃or Hal, where the radical R¹Or R²At least one of which always cannot be

H，

R³，R⁴In each case independently of one another, represents H, A, OA,

Hal，NO₂，NH₂a group of amino acids, NHA or NAA',

x represents imidazolyl or pyridyl, and

n represents 1; in Id, R¹And R²Together represent an alkylene group having 3 to 5 carbon atoms,

R³and R⁴Together represent-O-CH₂-CH₂-，-O-CH₂-O-or-O-CH₂-CH₂-O，

X represents imidazolyl or pyridyl, and

n represents 1; in Ie, R¹And R²Together represent an alkylene group having 3 to 5 carbon atoms,

R³，R⁴in each case independently of one another, represents H, A, OA,

Hal，NO₂，NH₂a group of amino acids, NHA or NAA',

x represents imidazolyl or pyridyl, and

n represents 1;

furthermore, the compounds of the formula I and the starting materials for their preparation can be prepared by methods known in the art under the known reaction conditions suitable for the abovementioned reactions, which are described in the literature (see, for example, standard publications such as Houben-Weyl, method in Organic Chemistry, Georg-Thieme-Verlag, Stuttgart). Variations of these methods may also be utilized which are well known in the art but not described in detail in the current textbook.

In the compounds of the formulae II, III and IV, R¹，R²，R³，R⁴X and n are as defined above, in particular as defined above as preferred.

If L is an OH group which is actively esterified, this group is preferably an alkylsulfonyloxy group having from 1 to 6 carbon atoms, preferably a methylsulfonyloxy group, or an arylsulfonyloxy group having from 6 to 10 carbon atoms, preferably a phenyl-or p-tolyl-sulfonyloxy group, and also preferably a 2-naphthalenesulfonyloxy group.

If desired, the starting materials may also be formed in situ so that they can be reacted directly in the next step without isolation from the reaction mixture to give the compounds of the formula I. On the other hand, the reaction may be carried out stepwise.

Compounds of the formula I in which X is bonded via N to a thienopyrimidine ring system are preferably prepared by reacting a compound of the formula II with a 5-to 7-membered unsaturated heterocycle having at least one NH group, the unsaturated heterocycle being unsubstituted or substituted by A, Hal or CF₃Mono-, di-or tri-substituted, and other CH in the unsaturated heterocycle₂The groups may also be replaced by NH, NA, S or O.

Some of the starting materials of formula II are known and, if they are not known, can be prepared using methods well known in the art.

Precursors of compounds of formula II can be prepared by cyclization and halogenation according to similar methods as described, for example, in journal of medicinal chemistry (j.med.chem.)24, 374 (1981). Followed by reaction with an aralkylamine to provide a compound of formula II.

In detail, the reaction of the compound of formula II with the NH containing heterocycle is carried out in the presence or absence of an inert solvent at a temperature of about-20 to about 150 ℃, preferably 20-100 ℃.

It is advantageous to add an acid binder, for example an alkali metal hydroxide, alkali metal carbonate, alkali metal bicarbonate, alkaline earth metal hydroxide, alkaline earth metal carbonate or alkaline earth metal bicarbonate, or other weak acid salts of alkali metals or alkaline earth metals, preferably potassium, sodium or calcium, or an organic base, for example triethylamine, dimethylamine or pyridine or quinoline or an excess of the amine component.

Examples of suitable inert solvents include hydrocarbons such as hexane, petroleum ether, benzene, toluene or xylene; chlorinated hydrocarbons such as trichloroethylene, 1, 2-dichloroethane, carbon tetrachloride, chloroform or dichloromethane; alcohols such as methanol, ethanol, isopropanol, n-propanol, n-butanol or tert-butanol; ethers such as diethyl ether, diisopropyl ether, Tetrahydrofuran (THF) or dioxane; glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether (methyl glycol or ethyl glycol) or ethylene glycol dimethyl ether (diglyme); ketones such as acetone or butanone; amides such as acetamide, dimethylacetamide or Dimethylformamide (DMF); nitriles such as acetonitrile; sulfoxides such as dimethyl sulfoxide (DMSO); nitro compounds such as nitromethane or nitrobenzene; esters such as ethyl acetate, or mixtures of the above solvents.

Furthermore, compounds of formula I wherein X is bonded to the thienopyrimidine ring system via C may be prepared by reacting a compound of formula III with a compound of formula IV. In general, the starting compounds of the formulae IV and V are known. But if they are unknown, they can be prepared using methods well known in the art.

For example, the compounds of formula III can be synthesized from thiophene derivatives and CN-substituted heterocycles as starting materials (Eur. J. Med. chem.)23, 453(1988)) by reaction with POCl₃And (3) reacting to obtain the product.

The reaction of the compound of formula III with the compound of formula IV is carried out under similar conditions as described for the reaction of the compound of formula II with the NH-containing heterocycle, including reaction time, temperature and solvent.

Furthermore, it is also possible to combine the radicals R in the compounds of the formula I³And/or R⁴Conversion into different radicals R³And/or R⁴For example, reduction of the nitro group to give an amino group (for example by hydrogenation in an inert solvent such as methanol or ethanol in the presence of Raney nickel (Raney Ni) or Pd/charcoal) or hydrolysis of the cyano group to give a COOH group.

Furthermore, the free amino group may be acylated with an acid chloride or acid anhydride in a conventional manner, or alkylated with an unsubstituted or substituted halogenated hydrocarbon in a conventional manner, suitably in an inert solvent such as dichloromethane or THF and/or in the presence of a base such as triethylamine or pyridine at-60 to +30 ℃.

The base of formula I may be converted to the corresponding acid addition salt by the use of an acid, for example by reacting equivalent amounts of the base and acid in an inert solvent such as ethanol, followed by evaporation to give the acid addition salt. In particular, suitable acids for this reaction are acids which form physiologically acceptable salts. For example, it is possible to use inorganic acids, such as sulfuric acid, nitric acid, hydrohalic acids, such as hydrochloric acid or hydrobromic acid, phosphoric acids, such as orthophosphoric acid, sulfamic acid, and furthermore organic acids, in particular aliphatic, cycloaliphatic, araliphatic, aromatic or heterocyclic mono-or polycarboxylic acids, sulfonic acids or sulfuric acids, such as formic acid, acetic acid, propionic acid, pivalic acid, diethylacetic acid, malonic acid, succinic acid, pimelic acid, fumaric acid, maleic acid, lactic acid, tartaric acid, malic acid, citric acid, gluconic acid, ascorbic acid, nicotinic acid, isonicotinic acid, methane-or ethanesulfonic acid, ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, naphthalenmono-and-disulfonic acid, dodecylsulfuric acid. Salts with physiologically unacceptable acids (e.g. picrates) are useful for isolating and/or purifying compounds of formula I.

On the other hand, if desired, the free base of formula I can be liberated from its salt using a base such as sodium hydroxide, sodium carbonate, potassium hydroxide or potassium carbonate.

The invention also relates to the use of a compound of formula I and/or a physiologically acceptable salt thereof for the manufacture of a medicament, in particular by a non-chemical route. They can be formulated in a suitable pharmaceutical form together with at least one excipient or auxiliary in solid, liquid and/or semi-liquid form and, if appropriate, with one or more active further active ingredients.

The invention also relates to the medicaments of formula I and the physiologically acceptable salts thereof which are useful as phosphodiesterase V inhibitors.

Furthermore, the present invention relates to pharmaceutical products comprising at least one compound of the formula I and/or physiologically acceptable salts thereof.

These products are useful as medicaments in human or veterinary medicine. Suitable excipients include organic or inorganic substances which are suitable for enteral (e.g. oral), parenteral or topical administration and which do not react with the novel compounds of the invention, for example water, vegetable oils, benzyl alcohols, alkylene glycols, polyethylene glycols, triacetin, gelatin, sugars such as lactose or starch, magnesium stearate, talc, vaseline. In particular, the dosage forms suitable for oral administration are tablets, pills, sugar-coated tablets, capsules, powders, granules, syrups, liquids or drops, in particular suppositories for rectal administration, in particular solutions for parenteral administration, preferably oil or aqueous solutions, and also suspensions, emulsions or implants, and topical administration include ointments, creams or powders. The novel compounds of the invention can also be lyophilized, the lyophilizates obtained being used for the preparation of, for example, injectable preparations. The above-mentioned products may be in sterile form and/or comprise adjuvants such as glidants (glidants), preservatives, stabilizers and/or wetting agents, emulsifiers, salts for improving the osmotic pressure, buffers, colorants, flavors and/or other active ingredients, such as one or more vitamins.

The compounds of the formula I and their physiologically acceptable salts are useful for controlling diseases, so that the cGMP (cyclic guanosine monophosphate) levels are increased, as a result of which inflammation and muscle relaxation can be inhibited or prevented. The compounds of the invention are particularly useful in the treatment of diseases of the cardiovascular system and are also suitable for the treatment of impaired sexual intercourse ability.

All temperatures given above and below are in degrees Celsius. In the following examples, "conventional work-up" means: if desired, water is added and, if desired, the pH is adjusted to 2-10, depending on the structure of the end product, and the mixture is then extracted with ethyl acetate or dichloromethane, the organic phase is separated off, dried over sodium sulfate and evaporated, and the residue is subsequently purified by chromatography on silica gel and/or by crystallization. Mass Spectrum (MS): EI (Electron impact ionization) M⁺

FAB (fast atom bombardment) (M + H)⁺

Example 1

3.02g of 3, 4-methylenedioxybenzylamine ("A") was added to a solution of 3.29g of 2, 4-dichloro-6-methylthioeno [2, 3-d ] pyrimidine in 80ml of methylene chloride, 1.52g of triethylamine was then added, and the mixture was stirred at room temperature for 12 hours. The solvent is removed and the work-up is carried out in a conventional manner. This gives 3.38g of 2-chloro-6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.162 ℃.

Similarly, by reacting "a" with the following compound, the following product can be obtained: reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine, m.p.222 °; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.148 °; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3-chloro-4-methoxybenzylamine with the following compound, the following product can be obtained: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (3-chloro-4-methoxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (3-chloro-4-methoxy benzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (3-chloro-4-methoxy benzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (3-chloro-4-methoxy benzylamino) thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3, 4-dimethoxybenzylamine with the following compounds, the following products can be obtained: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (3, 4-dimethoxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (3, 4-dimethoxy benzylamino) thieno [2, 3-d ] pyrimidine.

Similarly, by reacting benzylamine with the following compounds, the following products can be obtained: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4-benzylamino [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4-benzylaminothiophene [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4-benzylaminothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4-benzylaminothieno [2, 3-d ] pyrimidine.

Similarly, by reacting 4-fluoro-benzylamine with the following compounds, the following products can be prepared: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (4-fluorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3, 4-chlorobenzylamine with the following compound, the following product can be obtained: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (3, 4-dichlorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3-nitrobenzylamine with the following compound, the following product can be prepared: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (3-nitrobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3, 4-methylenedioxyphenethylamine with the following compounds, the following products can be prepared: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxyphenethylamino) [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3, 4-ethylenedioxybenzylamine with the following compounds, the following products can be obtained: reacting with 2, 4-dichloro-6-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-6-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5-methylthiophene [2, 3-d ] pyrimidine to obtain 2-chloro-5-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6, 7, 8-tetrahydro-4- (3, 4-ethylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cyclopenteno [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cyclopenteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-cycloheptene [1] benzothieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-cycloheptene-4- (3, 4-ethylenedioxy benzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-ethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-ethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, 6-trichlorothieno [2, 3-d ] pyrimidine to obtain 2, 6-dichloro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4, -5-trichloro-6-methyl thieno [2, 3-d ] pyrimidine to obtain 2, 5-dichloro-6-methyl-4- (3, 4-ethylenedioxy benzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-nitrothieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-nitro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2-chloro-5, 6-dimethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; reacting with 2, 4-dichloro-6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2-chloro-6-trifluoromethyl-4- (3, 4-ethylenedioxy benzylamino) thieno [2, 3-d ] pyrimidine.

Example 2

1.67g of 2-chloro-6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, 1.02g of imidazole and 2g of phenol were heated at 150 ℃ for 5 hours. After cooling, the residue is dissolved in dichloromethane and worked up in the customary manner. This gives 1.0g of 2- (imidazol-1-yl) -6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.248-250 ℃.

Similarly, by reacting imidazole with the 2-chloro-thieno [2, 3-d ] pyrimidine derivative substituted with an aralkylamino group at the 4-position obtained in example 1, the following compounds can be obtained: 2- (imidazol-1-yl) -5-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.238 °; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine, m.p.218 °; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.260 °; 2- (imidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.210 °; 2- (imidazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine methanesulfonate, m.p.201 °; 2- (imidazol-1-yl) -6-chloro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.245 °; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-chloro-4-methoxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclohepteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-ethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-chloro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dimethoxy-benzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-ethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-chloro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine, m.p.207 °; 2- (imidazol-1-yl) -5-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4-benzylamino [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclohepteno-4-benzylaminothio [2, 3-d ] pyrimidine, m.p.197 °; 2- (imidazol-1-yl) -6-ethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-chloro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (4-fluorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cycloheptene-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-ethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine, m.p.199 °; 2- (imidazol-1-yl) -6-chloro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dichlorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cycloheptene-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-ethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-chloro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-nitrobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclohepteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-ethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-chloro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxyphenethylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-chloro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-methyl-4- (3, 4-ethylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-ethylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-ethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-chloro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-nitro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -5, 6-dimethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (imidazol-1-yl) -6-trifluoromethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine;

similarly, by reacting pyrazole with the 2-chloro-thieno [2, 3-d ] pyrimidine derivative substituted with an aralkylamino group at the 4-position obtained in example 1, the following compounds can be obtained: 2- (pyrazol-1-yl) -6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine, m.p.210 °; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-chloro-4-methoxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclohepteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dimethoxy-benzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4-benzylamino [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cycloheptene-4-benzylaminothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (4-fluorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclohepteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dichlorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cycloheptene-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-nitrobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclohepteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxyphenethylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-methyl-4- (3, 4-ethylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-ethylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-ethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-chloro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5-chloro-6-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-nitro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -5, 6-dimethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (pyrazol-1-yl) -6-trifluoromethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine;

similarly, by reacting 1, 2, 4-triazole with the 2-chloro-thieno [2, 3-d ] pyrimidine derivative substituted with an aralkylamino group at the 4-position obtained in example 1, the following compounds can be obtained: 2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (3, 4-methylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, -2, 4-triazol-1-yl) -6-nitro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-chloro-4-methoxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dimethoxy-benzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4-benzylamino [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4-benzylaminothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (4-fluorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dichlorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, -2, 4-triazol-1-yl) -6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-nitrobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxyphenethylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-ethylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-ethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-chloro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5-chloro-6-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-nitro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -5, 6-dimethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (1, 2, 4-triazol-1-yl) -6-trifluoromethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine;

similarly, by reacting 2-methylimidazole with the 2-chloro-thieno [2, 3-d ] pyrimidine derivative substituted with an aralkylamino group at the 4-position obtained in example 1, the following compounds were obtained: 2- (2-methylimidazol-1-yl) -6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine, amorphous; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-chloro-4-methoxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (3-chloro-4-methoxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dimethoxy-benzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (3, 4-dimethoxy-benzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4-benzylamino [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4-benzylaminothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4-benzylaminothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4-benzylaminothio [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (4-fluorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine, m.p.199 °; 2- (2-methylimidazol-1-yl) -6-chloro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (4-fluorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-dichlorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (3, 4-dichlorobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3-nitrobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-methylenedioxyphenethylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (3, 4-methylenedioxyphenethylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-ethylenedioxybenzylamino) [1] benzothieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclopenteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-cyclohepteno-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-ethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-chloro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5-chloro-6-methyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-nitro-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -5, 6-dimethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; 2- (2-methylimidazol-1-yl) -6-trifluoromethyl-4- (3, 4-ethylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine;

example 3

5g of 2-amino-5-methyl-3-ethoxycarbonylthiophene and 2.7g of 3-cyanopyridine are dissolved in 40ml of dioxane and the solution is then aerated with HCl5 hours. Conventional work-up is subsequently carried out. 6g of 3, 4-dihydro-4-oxo-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine are obtained.

The keto group is replaced with Cl under standard conditions, with the formation of an aromatic pyridine ring. 18ml of POCl₃And 6g 3, 4-dihydro-4-oxo-2- (pyridin-3-yl) -6-methylthio [2, 3-d ]]The mixture of pyrimidines is boiled for 4 hours after addition of 1.8ml of N, N-dimethylaniline. Then, conventional post-treatment was carried out to obtain 5g of 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d]A pyrimidine.

In a similar manner to that described above,by reaction with 3-cyanopyridine followed by reaction with POCl₃The following products can be obtained from the following compounds: preparation of 4-chloro-2- (pyridin-3-yl) -5-methylthiothieno [2, 3-d ] from 2-amino-4-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] from 2-amino-4, 5, 6, 7-tetrahydro-3-ethoxycarbonylbenzothiophene]Benzothiophene [2, 3-d ]]Pyrimidine, m.p.143 °; preparation of 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] thiophene from 2-amino-4, 5-cyclopenteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -5, 6-cyclohepteno-thieno [2, 3-d ] from 2-amino-4, 5-cyclohepteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] from 2-amino-5-ethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] from 2-amino-5-chloro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthiothieno [2, 3-d ] from 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] from 2-amino-5-nitro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] from 2-amino-4, 5-dimethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] from 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene]A pyrimidine.

Similarly, by reaction with 5-cyanoisoxazole, followed by reaction with POCl₃The following products can be obtained from the following compounds: preparation of 4-chloro-2- (isoxazol-5-yl) -6-methylthiothieno [2, 3-d ] from 2-amino-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -5-methylthiothieno [2, 3-d ] from 2-amino-4-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] from 2-amino-4, 5, 6, 7-tetrahydro-3-ethoxycarbonylbenzothiophene]Benzothiophene [2, 3-d ]]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] from 2-amino-4, 5-cyclopenteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclo-thiophene from 2-amino-4, 5-cyclohepteno-3-ethoxycarbonylthiopheneHeptenothieno [2, 3-d ]]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] from 2-amino-5-ethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] thiophene from 2-amino-5-chloro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] from 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] from 2-amino-5-nitro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] from 2-amino-4, 5-dimethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] from 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene]A pyrimidine.

Analogously, by reaction with 2-cyanopyrazine, followed by reaction with POCl₃The following products can be obtained from the following compounds: preparation of 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] from 2-amino-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -5-methylthiothieno [2, 3-d ] from 2-amino-4-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] from 2-amino-4, 5, 6, 7-tetrahydro-3-ethoxycarbonylbenzothiophene]Benzothieno [2, 3-d ]]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] thiophene from 2-amino-4, 5-cyclopenteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclohepteno-thieno [2, 3-d ] from 2-amino-4, 5-cyclohepteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] from 2-amino-5-ethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] thiophene from 2-amino-5-chloro-3-ethoxycarbonylthiophene]A pyrimidine; preparing 4-chloro-2- (pyrazine-2-yl) -5-chloro-6-methylthiophene [2, 3-d ] from 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -6-nitrothieno [2, 3-d ] from 2-amino-5-nitro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] from 2-amino-4, 5-dimethyl-3-ethoxycarbonylthiophene]A pyrimidine; byPreparing 4-chloro-2- (pyrazine-2-yl) -6-trifluoromethyl thieno [2, 3-d ] by 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene]A pyrimidine.

Similarly, by reaction with 2-cyanopyridine followed by reaction with POCl₃The following products can be obtained from the following compounds: preparation of 4-chloro-2- (pyridin-2-yl) -6-methylthiothieno [2, 3-d ] from 2-amino-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -5-methylthiothieno [2, 3-d ] from 2-amino-4-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] from 2-amino-4, 5, 6, 7-tetrahydro-3-ethoxycarbonylbenzothiophene]Benzothieno [2, 3-d ]]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] thiophene from 2-amino-4, 5-cyclopenteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -5, 6-cyclohepteno-thieno [2, 3-d ] from 2-amino-4, 5-cyclohepteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] from 2-amino-5-ethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] from 2-amino-5-chloro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthiothieno [2, 3-d ] from 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] from 2-amino-5-nitro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] from 2-amino-4, 5-dimethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] from 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene]A pyrimidine.

Similarly, by reaction with 4-cyanopyridine followed by reaction with POCl₃The following products can be obtained from the following compounds: preparation of 4-chloro-2- (pyridin-4-yl) -6-methylthiothieno [2, 3-d ] from 2-amino-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -5-methylthiothieno [2, 3-d ] from 2-amino-4-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparing 4-chloro-2- (pyridine-4-yl) -5, 6 from 2-amino-4, 5, 6, 7-tetrahydro-3-ethoxycarbonylbenzothiophene,7, 8-tetrahydro [1]]Benzothieno [2, 3-d ]]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] thiophene from 2-amino-4, 5-cyclopenteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -5, 6-cyclohepteno-thieno [2, 3-d ] from 2-amino-4, 5-cyclohepteno-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] from 2-amino-5-ethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] from 2-amino-5-chloro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthiothieno [2, 3-d ] from 2-amino-4-chloro-5-methyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] from 2-amino-5-nitro-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] from 2-amino-4, 5-dimethyl-3-ethoxycarbonylthiophene]A pyrimidine; preparation of 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylthieno [2, 3-d ] from 2-amino-5-trifluoromethyl-3-ethoxycarbonylthiophene]A pyrimidine. Example 4

In analogy to example 1, by reacting 3, 4-methylenedioxybenzylamine with the following compounds, the following products can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine, with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine m.p.185 °; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; and reacting with 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3-chloro-4-methoxybenzylamine with the following compound, the following product can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-chloro-4-methoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-chloro-4-methoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-chloro-4-methoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-chloro-4-methoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4- (3-chloro-4-methoxy benzylamino) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3, 4-dimethoxybenzylamine with the following compounds, the following products can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dimethoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-dimethoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dimethoxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dimethoxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4- (3, 4-dimethoxy benzylamino) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine.

Similarly, by reacting benzylamine with the following compounds, the following products can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine m.p.189 °; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-3-yl) -4-benzylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-benzylamino-6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-benzylamino-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-benzylamino-5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-benzylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-benzylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-benzylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-benzylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-benzylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-benzylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-benzylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-benzylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-benzylamino-6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-5-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4-benzylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4-benzylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4-benzylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-benzylamino-6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-2-yl) -4-benzylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-benzylamino-6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyridin-4-yl) -4-benzylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4-benzylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-benzylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4-benzylamino-6-trifluoromethyl thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 4-fluorobenzylamine with the following compound, the following product can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (4-fluorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (4-fluorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -5-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -5, 6-cyclopentenothiopheno [ 2; 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4- (4-fluorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (4-fluorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (4-fluorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (4-fluorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4- (4-fluorobenzylamino) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3, 4-dichlorobenzylamine with the following compounds, the following products can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-dichlorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-dichlorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4- (3, 4-dichlorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-dichlorobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dioxobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-dichlorobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4- (3, 4-dichlorobenzylamino) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3-nitrobenzylamine with the following compound, the following product can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-3-yl) -4- (3-nitrobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3-nitrobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3-nitrobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -5-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4- (3-nitrobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4- (3-nitrobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3-nitrobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-2-yl) -4- (3-nitrobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3-nitrobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4- (3-nitrobenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3-nitrobenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine;

similarly, by reacting 3, 4-methylenedioxyphenethylamine with the following compounds, the following products can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthiophene [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; and reacting with 4-chloro-2- (pyridin-4-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-methylenedioxyphenethylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine.

Similarly, by reacting 3, 4-ethylenedioxybenzylamine with the following compounds, the following products can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4- (3, 4-ethylenedioxybenzylamino) -5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4- (3, 4-ethylenedioxy benzylamino) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine.

Similarly, by reacting phenethylamine with the following compounds, the following products can be obtained: reacting with 4-chloro-2- (pyridin-3-yl) -6-methylthiophene [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyridin-3-yl) -4-phenethylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-3-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-3-yl) -4-phenethylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-3-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-3-yl) -4-phenethylamino-6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-phenethylamino-6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-phenethylamino-5-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-phenethylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-phenethylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-phenethylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-phenethylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-phenethylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-phenethylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-phenethylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (isoxazol-5-yl) -4-phenethylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (isoxazol-5-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (isoxazol-5-yl) -4-phenethylamino-6-trifluoromethyl thieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenethylamino-6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-methylthiophene [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenylethylamino-5-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenethylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenethylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenethylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenethylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4-phenethylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenethylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4-phenethylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to obtain 2- (pyrazin-2-yl) -4-phenethylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyrazine-2-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyrazine-2-yl) -4-phenethylamino-6-trifluoromethyl thieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-2-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-2-yl) -4-phenethylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-2-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-2-yl) -4-phenethylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-2-yl) -6-trifluoromethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-2-yl) -4-phenethylamino-6-trifluoromethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-methylthiophene [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-6-methylthiophene [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-5-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-5, 6-cyclopentenothiopheno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-cycloheptenothieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-5, 6-cycloheptenothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-ethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-6-ethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -6-chlorothieno [2, 3-d ] pyrimidine to obtain 2- (pyridin-4-yl) -4-phenethylamino-6-chlorothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5-chloro-6-methylthioeno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-5-chloro-6-methylthioeno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-nitrothieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4-phenethylamino-6-nitrothieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridin-4-yl) -5, 6-dimethylthieno [2, 3-d ] pyrimidine to give 2- (pyridin-4-yl) -4-phenethylamino-5, 6-dimethylthieno [2, 3-d ] pyrimidine; reacting with 4-chloro-2- (pyridine-4-yl) -6-trifluoromethyl thieno [2, 3-d ] pyrimidine to obtain 2- (pyridine-4-yl) -4-phenethylamino-6-trifluoromethyl thieno [2, 3-d ] pyrimidine.

Example 5

Hydrogenation of a methanol solution of 2- (imidazol-1-yl) -6-methyl-4- (3-nitrobenzylamino) thieno [2, 3-d ] pyrimidine in the presence of Raney nickel (Raney nickel). The catalyst was then filtered off and the resulting solution was concentrated. Recrystallizing to obtain the 2- (imidazole-1-yl) -6-methyl-4- (3-aminobenzyl amino) thieno [2, 3-d ] pyrimidine.

Example 6

A solution of 6g of 2- (imidazol-1-yl) -6-methyl-4- (3-aminobenzylamino) thieno [2, 3-d ] pyrimidine and 0.5g of titanium tetrachloride in 100ml of methanol was treated with 1ml of freshly distilled acetaldehyde. Then 4g of sodium cyanoborohydride was added and the mixture was stirred for 30 hours. Semi-concentrated hydrochloric acid was added and the resulting mixture was worked up in a conventional manner to give 2- (imidazol-1-yl) -6-methyl-4- (3-N-ethylaminobenzylamino) thieno [2, 3-d ] pyrimidine.

Example 7

The following compounds were prepared analogously as described in example 2:

2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4- (3, 4-difluorobenzylamino) [1] benzothieno [2, 3-d ] pyrimidine, m.p.212 °;

2- (imidazol-1-yl) -5, 6-cyclopenteno-4-benzylaminothio [2, 3-d ] pyrimidine, m.p.221 °;

2- (imidazol-1-yl) -6-methyl-4-benzylaminothio [2, 3-d ] pyrimidine, m.p.241 °;

2- (imidazol-1-yl) -6-methyl-4- (3, 4-dimethoxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.217 °;

2- (imidazol-1-yl) -6-chloro-5-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.250 °;

2- (imidazol-1-yl) -5, 6, 7, 8-tetrahydro-4-benzylamino- [1] benzothieno [2, 3-d ] pyrimidine, m.p.190 °;

2- (1, 2, 4-triazol-1-yl) -6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.231 °;

2- (imidazol-1-yl) -6-isopropyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.192 °;

2- (imidazol-1-yl) -6-propyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine, m.p.183 °.

The following examples relate to pharmaceutical products. Example A: small bottle agent (vitamins)

100g of the active ingredient of the formula I and 5g of disodium hydrogen phosphate are dissolved in 3l of redistilled water, adjusted to pH6.5 with 2N hydrochloric acid, sterile-filtered, injected into vials, lyophilised under sterile conditions and sealed in sterile form. Each vial contained 5mg of active ingredient.

Example B: suppository

20g of the active ingredient of the formula I are melted together with 100g of soya lecithin and 1400g of cocoa butter, and the mixture is poured into a mould and allowed to cool. Each suppository contains 20mg of active ingredient.

Example C: solutions of

By mixing 1g of active ingredient of formula I, 9.38g of NaH₂PO₄·2H₂O、28.48gNa₂HPO₄·12H₂A solution was prepared by dissolving O and 0.1g of benzalkonium chloride in 940ml of redistilled water. The pH of the solution was adjusted to 6.8, added to a volume of 1l and radiation sterilized. The solution can be used in the form of eye drops.

Example D: ointment formulation

500mg of active ingredient of the formula I are mixed with 99.5g of vaseline under sterile conditions.

Example E: tablet formulation

A mixture of 1kg of active ingredient of the formula I, 4kg of lactose, 1.2kg of potato starch, 0.2kg of talc and 0.1kg of magnesium stearate is compressed in the usual manner in such a way that each tablet contains 10mg of active ingredient. Example F: sugar-coated tablet

The mixture is compressed as described in example E, and the tablets obtained are subsequently coated in a conventional manner with a coating consisting of sucrose, potato starch, talc, tragacanth and colorant.

Example G: capsule preparation

In a conventional manner, 2kg of active ingredient of the formula I are filled into hard gelatin capsules, so that each capsule contains 20mg of active ingredient.

Example H: ampoule agent

A solution of 1kg of the active ingredient of the formula I in 60l of redistilled water is sterile-filtered and injected into ampoules, which are then lyophilised under sterile conditions and sealed in sterile form. Each ampoule contains 10mg of active ingredient. Example I: aerosol for inhalation

14g of active ingredient of the formula I are dissolved in 10l of isotonic NaCl solution and the solution obtained is introduced into a spray container which is operated on a commercial pump. The solution can be sprayed into the mouth or nasal cavity. The amount per operation (about 0.1ml) corresponds to a dose of about 0.14 mg.

Claims (6)

1. A compound of formula I:wherein R is¹，R²In each case independently of one another, represents H, A or Hal, where R¹Or R²

One of them always cannot be hydrogen, R¹And R²And together also represents an alkylene radical having 3 to 5 carbon atoms, R³，R⁴In each case independently of one another, represents H, OA or Hal, R³And R⁴And also togetherrepresents-O-CH₂-O-or-O-CH₂-CH₂-O-, a represents an alkyl group having 1 to 6 carbon atoms, X represents 1-imidazolyl, 2-methyl-imidazolyl, pyrazolyl, 1, 2, 4-tris

Oxazol-1-yl or 3-pyridyl, Hal represents F, Cl, Br or I, and n represents 1, with the proviso that: if R is¹、R²In each case independently of one another H, A or Hal, and R¹Or R²Is not always hydrogen, then R³And R⁴Is not H.

2. A compound of formula I according to claim 1, which is: (a)2- (1-imidazolyl) -6-methyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; (b)2- (1-imidazolyl) -5, 6-dimethyl-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; (c)2- (1-imidazolyl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; (d)2- (1-imidazolyl) -5-chloro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; (e)2- (1-imidazolyl) -6-chloro-4- (3, 4-methylenedioxybenzylamino) thieno [2, 3-d ] pyrimidine; (f)2- (1, 2, 4-triazol-1-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; (g)2- (pyrazol-1-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine; (h)2- (pyridin-3-yl) -4- (3, 4-methylenedioxybenzylamino) -5, 6, 7, 8-tetrahydro [1] benzothieno [2, 3-d ] pyrimidine.

3. A process for the preparation of compounds of the formula I according to claim 1 and salts thereof, a) for compounds of the formula I according to claim 1 and salts thereof in which X is bonded via N, characterized in that a compound of the formula II:wherein R is¹，R²，R³，R⁴And n is as defined above, and L represents Cl, Br, OH, SCH₃Or reactive esterified OH groups with at least one NH groupReaction of a 5-7 membered unsaturated heterocycle wherein the unsaturated heterocycle is unsubstituted or substituted by A, Hal or CF₃Mono-, di-or tri-substituted, and other CH in the unsaturated heterocycle₂May also be replaced by NH, NA, S or O,

or b) for compounds of the formula I according to claim 1, wherein X is bonded via C, and salts thereof, characterized in that a compound of the formula III:wherein

R¹，R²And X is as defined above, and L is Cl, Br, OH, SCH₃Or a reactive esterified OH group with a compound of formula IV:wherein R is³，R⁴And n is as defined above, and n is,

or c) the process is characterized in that the radical R in the compounds of the formula I is reacted in the following manner¹，R²，R³And/or R⁴Conversion into different radicals R¹，R²，R³And/or R⁴: reducing the nitro group, converting a primary or secondary amino group into an alkylated amine by reductive amination or acylating such an amino group, and/or which process is characterized in that a basic compound of the formula I is converted into a salt thereof by treatment with an acid.

4. Pharmaceutical preparation, characterized in that it comprises at least one compound of the formula I according to 1 and/or a physiologically acceptable salt thereof.

5. The use of compounds of the formula I according to claim 1 and their physiologically acceptable salts for the production of medicaments for the prophylaxis and treatment of diseases of the cardiovascular system and for the treatment of impaired sexual intercourse.

6. The use of compounds of the formula I according to claim 1 and their physiologically acceptable salts as phosphodiesterase V inhibitors.