DE870558C - Process for the preparation of 2-aminopyrimidine - Google Patents
Process for the preparation of 2-aminopyrimidineInfo
- Publication number
- DE870558C DE870558C DEF2762D DEF0002762D DE870558C DE 870558 C DE870558 C DE 870558C DE F2762 D DEF2762 D DE F2762D DE F0002762 D DEF0002762 D DE F0002762D DE 870558 C DE870558 C DE 870558C
- Authority
- DE
- Germany
- Prior art keywords
- amino
- aminopyrimidine
- dichloropyrimidine
- potassium carbonate
- preparation
- 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
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- JPZOAVGMSDSWSW-UHFFFAOYSA-N 4,6-dichloropyrimidin-2-amine Chemical compound NC1=NC(Cl)=CC(Cl)=N1 JPZOAVGMSDSWSW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DBGFGNCFYUNXLD-UHFFFAOYSA-N 4-chloropyrimidin-2-amine Chemical compound NC1=NC=CC(Cl)=N1 DBGFGNCFYUNXLD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 101100285402 Danio rerio eng1a gene Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- ORBGDGDAQVZFMQ-UHFFFAOYSA-N o-pyrimidin-2-ylhydroxylamine Chemical class NOC1=NC=CC=N1 ORBGDGDAQVZFMQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical class C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
Verfahren zur Herstellung von 2-Aminopyrimidin Das 2Aminopyrimidin ist ein wichtiges Zwischenprodukt für die Herstellung des als Chemotherapeutikum gebrauchten 2 - (p - Aminobenzolsulfonamido)-pyrimidins. Es läßt sich nach B ü t t n e r (Berichte der deutschen chemischen Gesellschaft, 36 [19o3], S.2227) dadurch gewinnen, daß man 2-Amino-4, 6-dichlorpyrimidin durch Kochen mit Zinkstaub in wässeriger Lösung entchlort. Nach Roblin, Williams, Winnek und Eng-1 i s h (Journal of the American Chemical Society, 62 [19401, S. 2002) wird es dargestellt, indem man 2-Amino-4-chlorpyrimidin in methanolischer oder äthanolischer Lösung in Gegenwart von Bariumoxyd und mit Hilfe von Palladiumhydroxyd-Calciumcarbonat katalytisch entchlort.Process for the preparation of 2-aminopyrimidine The 2-aminopyrimidine is an important intermediate for the manufacture of the chemotherapeutic agent used 2 - (p - aminobenzene sulfonamido) pyrimidines. It can be traced back to B ü t t n e r (reports of the German chemical society, 36 [19o3], p.2227) thereby win that you get 2-amino-4, 6-dichloropyrimidine by boiling with zinc dust in aqueous Solution dechlorinated. According to Roblin, Williams, Winnek and Eng-1 i s h (Journal of the American Chemical Society, 62 [19401, p. 2002) it is represented by adding 2-amino-4-chloropyrimidine in methanolic or ethanolic solution in the presence of barium oxide and with Catalytically dechlorinated with the help of palladium hydroxide calcium carbonate.
Weiterhin ist in der amerikanischen Patentschrift 2 242 o79 ein Verfahren zur Herstellung von 2-Aminopyrimidin beschrieben, gemäß dem 2 .Amino-q.-chlorpyrimidin in wässeriger Dispersion mit fein verteiltem metallischem Zink unter alkalischen Bedingungen behandelt wird.In addition, US Pat. No. 2,242,079 describes a method for the preparation of 2-aminopyrimidine, according to the 2 .amino-q.-chloropyrimidine in aqueous dispersion with finely divided metallic zinc under alkaline Conditions is treated.
Es wurde gefunden, daß man 2-Aminopyrimidin besonders vorteilhaft gewinnen kann, wenn man 2-Amino-4, 6-dichlorpyrimidin in geeigneten Lösungsmitteln in Gegenwart von Natriumcarbonat oder Kaliumcarbonat mit Hilfe von Metallkatalysatoren, die auf geeigneten Trägermassen niedergeschlagen sein können, katalytisch entchlort.It has been found that 2-aminopyrimidine is particularly advantageous can win if you 2-amino-4, 6-dichloropyrimidine in suitable solvents in the presence of sodium carbonate or potassium carbonate with the help of metal catalysts, which can be deposited on suitable carriers, catalytically dechlorinated.
Der besondere Vorteil dieser Arbeitsweise besteht darin, daß zur Bindung der bei der Reaktion frei werdenden Salzsäure ein verhältnismäßig schwaches und gut wasserlöslichesAlkali verwendet wird, das zur Bildung eines stabilen und wasserlöslichen Bicarbonates befähigt ist. Das 2 Amino-4, 6-dichlorpyrimidin ist noch mehr als das 2-Amino-4-chlorpyrimidin geneigt, durch Hydrolyse in Aminooxypyrimidine überzugehen, deshalb sind Ätzalkalien, wie Bariumoxyd, Natronlauge oder Kalilauge, weniger geeignet. Auch Erdalkalicarbonate, die sehr wenig wasserlöslich sind und nur wenig wasserlösliche Bicarbonate zu bilden vermögen, sind weniger geeignet, da sie infolge dieser Schwerlöslichkeit zu langsam reagieren und ungenügend in Bicarbonate übergehen. Im Gegensatz dazu erhält man bei Benutzung von Natriumcarbonat oder Kaliumcarbonat eine außerordentlich rasche Enthalogenierung und eine praktisch quantitative Ausbeute, besonders wenn man mindestens vier Äquivalente Natriumcarbonat bzw..Kaliumcarbonat anwendet, so daß bis zum Schluß der Reaktion alle Kohlensäure als Bicarbonat gebunden bleibt und den Partialdruck des Wasserstoffs -im Hydriergefäß nicht herabmindern kann. , Dabei zeigt Kaliumcarbonat gegenüber Natriumcarbonat noch gewisse Vorteile. Da das 2--Amino-4,6-dichlorpyrimidin in Wasser sehr wenig löslich ist und deshalb in einem geeigneten Lösemittel, wie z. B. Methanol oder Äthanol, angewendet wird, kann mit Kaliumcarbonat wesentlich konzentrierter gearbeitet werden, da durch die Kabiumcarbonatlösung wesentlich weniger Wasser in die Reaktionsmischung eingebracht wird als durch die Natriumcarbonatlösung und damit -die zur Herstellung einer homogenen Lösung nötige Menge des organischen Lösemittels geringer gehalten werden kann.The particular advantage of this mode of operation is that it is used for binding the hydrochloric acid released during the reaction is a relatively weak and well water-soluble alkali is used, which forms a stable and water-soluble Bicarbonates is capable. The 2 amino-4, 6-dichloropyrimidine is even more inclined than the 2-amino-4-chloropyrimidine, by hydrolysis into aminooxypyrimidines to pass over, therefore caustic alkalis, such as barium oxide, caustic soda or potassium hydroxide, less suitable. Also alkaline earth carbonates, which are very little soluble in water and are able to form only slightly water-soluble bicarbonates, are less suitable because they react too slowly as a result of this poor solubility and insufficiently in bicarbonates pass over. In contrast, if you use sodium carbonate or potassium carbonate, you get it an extremely rapid dehalogenation and a practically quantitative yield, especially if you have at least four equivalents of sodium carbonate or potassium carbonate applies so that all carbonic acid is bound as bicarbonate until the end of the reaction and do not reduce the partial pressure of the hydrogen in the hydrogenation vessel can. , Potassium carbonate still has certain advantages over sodium carbonate. Because the 2 - amino-4,6-dichloropyrimidine is very sparingly soluble in water and therefore in a suitable solvent, such as. B. methanol or ethanol is used, Potassium carbonate can be used in a much more concentrated manner, as the Kabiumcarbonatlösung introduced significantly less water into the reaction mixture is considered by the sodium carbonate solution and thus -that to produce a homogeneous Solution required amount of the organic solvent can be kept lower.
Beispiel s In einem Hydriergefäß werden 3289 2@Amino-¢, 6-dichlorpyrimidin, das zweckmäßig in bekannter Weise nach den Angaben von @Bi ü t t n e r .durch Vakuumsublimation gereinigt ist, in iooo ccm Methanol suspendiert und mit einer Lösung von 700 g Kaliumcarbonat in 700 ccm Wasser vermischt. Sodann werden ioo g Calciumcarbonat, auf dem o,9 g Palladium in Form seines Hydroxydes niedergeschlagen ist, zugegeben. Die Mischung wird ohne äußere Wärmezufuhr und ohne Merdruck in einer Wasserstoffatmosphäre geschüttelt. Sie erwärmt sich dabei rasch von selbst und nimmt in wenigen Stunden die ¢ 9-Mol entsprechende Menge Wasserstoff auf. Die Reaktionsmischung wird abgesaugt und :der Niederschlag mif Methanol nachgewaschen. Durch Eindampfen des Filtrats im Vakuum erhält man das rohe 2iAminopyrimidin, das von beigemengten anorganischen Salzen durch Lösen in Methylenchlori-d und Abdampfen des Lösemittels befreit wird. Es kann durch Sublimation im Vakuum völlig rein mit .dem Schmelzpunkt 128° erhalten werden. Die Ausbeute beträgt dann etwa 9o% der Theorie. Der Katalysator kann nach Entfernen der Kaliumsalze durch Ausziehen mitWasser für weitere Hydrierungen gebraucht werden.Example 2 @ s are 3289 amino ¢, 6-dichloropyrimidine, the appropriate above in a known manner according to the data of @Bi ttner .by vacuum sublimation is cleaned in a hydrogenation vessel, suspended in iooo cc of methanol and treated with a solution of 700 g of potassium carbonate in 700 cc of water mixed. 100 g of calcium carbonate, on which 0.9 g of palladium has precipitated in the form of its hydroxide, are then added. The mixture is shaken in a hydrogen atmosphere without external heat supply and without pressure. It heats up quickly by itself and takes up the ¢ 9 mol corresponding amount of hydrogen in a few hours. The reaction mixture is filtered off with suction and: the precipitate is washed with methanol. Evaporation of the filtrate in vacuo gives the crude 2i-aminopyrimidine, which is freed from added inorganic salts by dissolving in methylene chloride and evaporating the solvent. It can be obtained completely pure with a melting point of 128 ° by sublimation in a vacuum. The yield is then about 90% of theory. After the potassium salts have been removed by extraction with water, the catalyst can be used for further hydrogenations.
Beispiel e 1649 2-Amino-4, frdichlorpyrimidin werden in einem Hydriergefäß mit iooo com Äthanol übergossen und mit einer Lösung von 22o g wasserfreiem Natriumcarbonat in iooo ccm warmem Wasser vermischt. Nach ,Zugabe von ioog Calciumcarbonat, das zuvor mit 0,39 Palladiumchlorür umgesetzt wurde, schüttelt man ohne Wärmezufuhr mit Wasserstoff von gewöhnlichem Druck. Nach Aufnahme von ¢81 Wasserstoff kommt die Hydrierung zum Stillstand. Die Flüssigkeit wird abfiltriert und der Niederschlag mit wässerigem Äthanol gewaschen. Das Filtrat wird mit Salzsäure kongosauer gemacht und im Vakuum zur Trockne gedampft. Der Rückstand wird in möglichst wenig Wasser aufgelöst und mit konzentrierter Kaliumcarbonatlösung alkalisch gemacht, wobei das 2-Aminopyrimidin auskristallisiert. iDer Katalysator kann auch hier wieder verwendet werden.Example e 1649 2-Amino-4, frdichloropyrimidine are poured over 1000000 ethanol in a hydrogenation vessel and mixed with a solution of 220 g of anhydrous sodium carbonate in 10000 cc of warm water. After adding 10 og calcium carbonate, which has previously been reacted with 0.39 palladium chloride, it is shaken with hydrogen at normal pressure without supplying heat. After the absorption of ¢ 81 hydrogen, the hydrogenation comes to a standstill. The liquid is filtered off and the precipitate is washed with aqueous ethanol. The filtrate is made Congo acidic with hydrochloric acid and evaporated to dryness in vacuo. The residue is dissolved in as little water as possible and made alkaline with concentrated potassium carbonate solution, the 2-aminopyrimidine crystallizing out. iThe catalyst can also be used again here.
Der Palladiumkatalysator kann als Trägersubstanz an Stelle von Calciumcarbonat auch andere Substanzen, z. B. Bariumsulfat oder Tierkohle, enthalten. Als Lösungsmittel können statt Äthanol auch höhere Alkohole, ferner Aceton oder Tetrahydrofuran Verwendung finden; endlich kann man den Palladiumkatalysator durch einen Platinkatalysator ersetzen.The palladium catalyst can be used as a carrier in place of calcium carbonate also other substances, e.g. B. barium sulfate or animal charcoal. As a solvent Instead of ethanol, higher alcohols, acetone or tetrahydrofuran can also be used Find; Finally, the palladium catalyst can be replaced by a platinum catalyst substitute.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF2762D DE870558C (en) | 1942-09-06 | 1942-09-06 | Process for the preparation of 2-aminopyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF2762D DE870558C (en) | 1942-09-06 | 1942-09-06 | Process for the preparation of 2-aminopyrimidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE870558C true DE870558C (en) | 1953-03-16 |
Family
ID=7083450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF2762D Expired DE870558C (en) | 1942-09-06 | 1942-09-06 | Process for the preparation of 2-aminopyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE870558C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185690A (en) * | 1959-06-03 | 1965-05-25 | Hoffmann La Roche | 2-chloro-4-amino-5-fluoropyrimidine |
-
1942
- 1942-09-06 DE DEF2762D patent/DE870558C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185690A (en) * | 1959-06-03 | 1965-05-25 | Hoffmann La Roche | 2-chloro-4-amino-5-fluoropyrimidine |
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