CH284261A - Process for the preparation of 4-chloro-2-amino-6-methylpyrimidine-1-methobromide. - Google Patents
Process for the preparation of 4-chloro-2-amino-6-methylpyrimidine-1-methobromide.Info
- Publication number
- CH284261A CH284261A CH284261DA CH284261A CH 284261 A CH284261 A CH 284261A CH 284261D A CH284261D A CH 284261DA CH 284261 A CH284261 A CH 284261A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- methylpyrimidine
- amino
- methobromide
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 229940102396 methyl bromide Drugs 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000002690 trypanocidal agent Substances 0.000 claims description 2
- NPTGVVKPLWFPPX-UHFFFAOYSA-N 2-amino-4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(N)=N1 NPTGVVKPLWFPPX-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<B>Verfahren zur Herstellung von</B> 4-Chlor-2-amino-6-methylpyrimidin-l-methobromid. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung von 4-Chlor- 2 -amino - 6 -methylpyrimidin-1-methobromid, welches dadurch gekennzeichnet ist, dass 4-Chlor-2-aniino-6-niethylpyrimidin mit Me- thylbromid zur Reaktion gebracht wird.
Die Reaktion kann durch Erhitzen der ver einigten Reaktionsteilnehmer in einem geschlos senen Gefäss, zweckmässigerweise in Gegen wart eines Lösungsmittels, wie z. B. ,B-Äthoxy- äthanol,Äthanol, Nitrobenzol, Nitroäthan oder Äthylessigester, ausgeführt werden.
Das neue quaternäre Salz eignet sich für die Herstellung von Chemotherapeutika und insbesondere von neuen trypanoziden Mitteln. Es kann, wenn gewünscht, nacheinfachen Verfahren der doppelten Umsetzung in qua- ternäre Salze mit einem andern Anion über geführt werden.
Im folgenden Beispiel sollen unter Teile Gewichtsteile verstanden werden. Beispiel: 14,4 Teile 4-Chlor-2-ainino-6-metliylpy rimi- din, 40 Teile Methylalkohol und 12 Teile Me- thylbroniid werden gemischt und in einem ge schlossenen Gefäss während 10 Stunden bei 125 bis 1.30 C erhitzt. Das Reaktionsgemisch wird abgekühlt und eingedampft, worauf der feste Rückstand mit 50 Teilen kaltem Wasser extrahiert und filtriert wird. Das Filtrat wird mit 30 Teilen Natriumbromid versetzt.
Man filtriert das Gemisch und lässt den festen Rückstand aus Wasser auskristallisieren, wo bei man 4-Chlor-2-amino-6-methylpyrimidin-l- methobromid in Form farbloser Platten vom Smp. 275 C (Zersetzung) erhält.
<B> Process for the preparation of </B> 4-chloro-2-amino-6-methylpyrimidine-1-methobromide. The present invention relates to a process for the preparation of 4-chloro-2-amino-6-methylpyrimidine-1-methobromide, which is characterized in that 4-chloro-2-aniino-6-niethylpyrimidine is reacted with methyl bromide becomes.
The reaction can be carried out by heating the united reactants in a closed vessel, conveniently in the presence of a solvent such as. B., B-ethoxy ethanol, ethanol, nitrobenzene, nitroethane or ethyl acetate, are carried out.
The new quaternary salt is suitable for the production of chemotherapeutic agents and in particular of new trypanocidal agents. If desired, it can be converted into quaternary salts with a different anion by a simple process of double conversion.
In the following example, parts are to be understood as parts by weight. Example: 14.4 parts of 4-chloro-2-ainino-6-methylpyimidine, 40 parts of methyl alcohol and 12 parts of methylbroniid are mixed and heated in a closed vessel at 125 to 1.30 C for 10 hours. The reaction mixture is cooled and evaporated, whereupon the solid residue is extracted with 50 parts of cold water and filtered. 30 parts of sodium bromide are added to the filtrate.
The mixture is filtered and the solid residue is left to crystallize from water, giving 4-chloro-2-amino-6-methylpyrimidine-1-methobromide in the form of colorless plates with a melting point of 275 ° C. (decomposition).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB284261X | 1947-08-22 | ||
| CH270254T | 1948-08-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH284261A true CH284261A (en) | 1952-07-15 |
Family
ID=25731153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH284261D CH284261A (en) | 1947-08-22 | 1948-08-21 | Process for the preparation of 4-chloro-2-amino-6-methylpyrimidine-1-methobromide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH284261A (en) |
-
1948
- 1948-08-21 CH CH284261D patent/CH284261A/en unknown
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