GB1174165A - Production of Pyrimidines Bearing a Halogen as Substituent in the 5-Position - Google Patents
Production of Pyrimidines Bearing a Halogen as Substituent in the 5-PositionInfo
- Publication number
- GB1174165A GB1174165A GB1792667A GB1792667A GB1174165A GB 1174165 A GB1174165 A GB 1174165A GB 1792667 A GB1792667 A GB 1792667A GB 1792667 A GB1792667 A GB 1792667A GB 1174165 A GB1174165 A GB 1174165A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- group
- general formula
- carbon atoms
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000005843 halogen group Chemical group 0.000 title abstract 3
- 150000003230 pyrimidines Chemical group 0.000 title abstract 3
- 125000001424 substituent group Chemical group 0.000 title abstract 3
- 229910052736 halogen Inorganic materials 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 aralkyl radical Chemical class 0.000 abstract 5
- 150000005840 aryl radicals Chemical group 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001409 amidines Chemical class 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 150000005697 5-halopyrimidines Chemical class 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000005599 propionic acid derivatives Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,174,165. Pyrimidine derivatives. BADISCHE ANILIN - & SODA - FABRIK A.G. 19 April, 1967 [20 April, 1966 (3)], No. 17926/67. Heading C2C. 5-Halo-pyrimidine derivatives having the general formula wherein R<SP>1</SP> is a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl radical or an aryl radical bearing one or more substituents which are inert under the reaction conditions; X is a halogen atom; and Y is (a) a -NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>3</SP> and R<SP>4</SP> are each a hydrogen atom, an alkyl, cycloalkyl or aralkyl radical or an aryl radical optionally substituted by one or more substituents which are inert under the reaction conditions or together form an alkylene radical having 2 to 6 carbon atoms in which one methylene group may be replaced by an oxygen or sulphur atom or by an or (in which R<SP>5</SP> is an alkyl, cycloalkyl or phenyl radical) group; or (b) a -NR<SP>2</SP>NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>2</SP> is a hydrogen atom or a methyl group and R<SP>3</SP> and R<SP>4</SP> are as defined above, are prepared by reaction of a 4,5-dihalopyrimidine of the general formula with a compound of the Formula HY or an alkali metal or alkaline earth metal salt thereof, at 30-200‹ C. Pyrimidine derivatives of the first general formula above wherein R<SP>1</SP> is an aryl radical having 6 to 12 carbon atoms; X is a chlorine or bromine atom; and Y is (a) a -NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>3</SP> and R<SP>4</SP> are each a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 6 to 12 carbon atoms, an aralkyl radical having 7 to 9 carbon atoms or an aryl group, or together form an alkylene radical having 2 to 6 carbon atoms in which one methylene group may be replaced by an oxygen atom; or (b) a-NR<SP>2</SP>- NR<SP>3</SP>R<SP>4</SP> radical, in which R<SP>2</SP> is a hydrogen atom or a methyl group and R<SP>3</SP> and R<SP>4</SP> are as defined above in this paragraph, are novel compounds. 4,5 - Dihalopyrimidines of the second general formula above are prepared by reaction of (i) an acrylic acid derivative of the general formula wherein R<SP>6</SP> is a halogen atom or an alkoxy group, R<SP>7</SP> is an alkoxy group or a -NR<SP>8</SP>R<SP>9</SP> group in which R<SP>8</SP> and R<SP>9</SP> are each a hydrogen atom or a C 1-4 alkyl group; or (ii) a propionic acid derivative of the general formula wherein R<SP>7</SP> and X are as defined above and R<SP>10</SP> and R<SP>11</SP> are alkyl groups, with an amidine of the general formula or an acid addition salt thereof from which the amidine can be liberated by reaction with a base, at 30-120‹ C. in the presence of a base; and reaction of the resulting 5-halo-4-hydroxypyrimidine of the general formula with phosgene, oxalyl chloride, a chloride, bromide or iodide of trivalent or pentavalent phosphorus, or an oxychloride or oxybromide of pentavalent phosphorus or of tetravalent or hexavalent sulphur at 30-200‹ C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0086751 | 1966-04-20 | ||
| DEB0086749 | 1966-04-20 | ||
| DEB0086748 | 1966-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1174165A true GB1174165A (en) | 1969-12-17 |
Family
ID=27209348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1792667A Expired GB1174165A (en) | 1966-04-20 | 1967-04-19 | Production of Pyrimidines Bearing a Halogen as Substituent in the 5-Position |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1174165A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2158081A1 (en) * | 1971-10-28 | 1973-06-15 | Delalande Sa |
-
1967
- 1967-04-19 GB GB1792667A patent/GB1174165A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2158081A1 (en) * | 1971-10-28 | 1973-06-15 | Delalande Sa |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |