CH299944A - Process for the preparation of a pyrimidine derivative. - Google Patents
Process for the preparation of a pyrimidine derivative.Info
- Publication number
- CH299944A CH299944A CH299944DA CH299944A CH 299944 A CH299944 A CH 299944A CH 299944D A CH299944D A CH 299944DA CH 299944 A CH299944 A CH 299944A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- para
- preparation
- pyrimidine derivative
- bromophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- 150000003230 pyrimidines Chemical class 0.000 title description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229960004198 guanidine Drugs 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- KBODHHFICHANMJ-UHFFFAOYSA-N 2-(4-bromophenyl)-3-oxobutanenitrile Chemical compound CC(=O)C(C#N)C1=CC=C(Br)C=C1 KBODHHFICHANMJ-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation d'un dérivé de la pyrimidine. La présente invention se rapporte à un procédé de préparation d'un composé nou veau, la 2,4-diamino-5-para.-bromophényl-6- méthyl-pyrimidine.
Il a été trouvé que ce composé possède des qualités précieuses pour le traitement de la malaria humaine. On le prépare, selon la pré sente invention, en faisant réagir un f-alcoyl- oxy-p-mét.hyl-a-para-bromophényl-acrylonitrile avec de la gnanidine. Ce composé a un point de fusion de 262-265 C.
L'aerylonitrile susmentionné peut être pré paré en partant @ d'a-acétylya-para-bromophé- nyl-acétonitrile en faisant réagir ce dernier avec un agent d'alcoylation, par exemple le di- azaméthane. Comme ?e groupe alcoyle (R) contenu dans le groupe alcoyloxy n'entre pas dans le produit final, tout groupe alcoyle inférieur convenable peut être employé.
Ces réactions s'effectuent. comme indiqué ci- après:
EMI0001.0022
Exemple: Le produit de départ a été préparé comme suit ; On a. traité de l'a-acétyl-a-para-bromophé- nyl-acétonitrile (11,3 g) avec du diazométhane (préparé avec 10 g de nitrosométhylurée), dans de l'éther (250 ml). Après repos pen dant une nuit à la température ordinaire, l'éther a été évaporé et remplacé par de l'al cool absolu (50 ml).
On a alors ajouté une solution de guani- dine (préparée à partir de 4,6 g de chlor- hydrate de guanidine) et 1,2 g de sodium dans 50 ml d'alcool, et on a chauffé le mélange <I>avec</I> reflux pendant 12 heures au bain de vapeur. Puis on a évaporé l'alcool, ajouté une solution 5 N de soude caustique, et filtré le mélange. Le résidu a été purifié par dissolu tion dans de l'acide acétique aqueux dilué, traitement avec du noir animal et reprécipi- tation avec de la soude caustique.
Après re- cristallisation, la 2,4-diamino-5-para: bromo- phény 1-6-méthyl-pyrimidine avait un point de fusion de<B>262-2650</B> C.
Le même composé a été préparé de façon semblable par condensation de guanidine avec du P-éthoxy-p,-méthyl-a-para-bromophényl- acrylonitrile. Après purification, comme ci- dessus, le composé fondait. à 262-265 C.
Process for the preparation of a pyrimidine derivative. The present invention relates to a process for the preparation of a new compound, 2,4-diamino-5-para.-bromophenyl-6-methyl-pyrimidine.
This compound has been found to have valuable qualities for the treatment of human malaria. It is prepared according to the present invention by reacting an β-alkyl-oxy-p-methyl-α-para-bromophenyl-acrylonitrile with gnanidine. This compound has a melting point of 262-265 C.
The above-mentioned aerylonitrile can be prepared starting from α-acetylya-para-bromophenyl-acetonitrile by reacting the latter with an alkylating agent, for example di-azamethane. Since the alkyl group (R) contained in the alkyloxy group does not enter into the final product, any suitable lower alkyl group can be employed.
These reactions take place. as indicated below:
EMI0001.0022
Example: The starting material was prepared as follows; We have. treated α-acetyl-α-para-bromophenyl-acetonitrile (11.3 g) with diazomethane (prepared with 10 g of nitrosomethylurea), in ether (250 ml). After standing overnight at room temperature, the ether was evaporated and replaced with absolute alcohol (50 ml).
A solution of guanidine (prepared from 4.6 g of guanidine hydrochloride) and 1.2 g of sodium in 50 ml of alcohol was then added, and the mixture was heated with </I> reflux for 12 hours in the steam bath. Then the alcohol was evaporated, a 5N solution of caustic soda added, and the mixture filtered. The residue was purified by dissolving in dilute aqueous acetic acid, treating with animal charcoal and reprecipitating with caustic soda.
After recrystallization, 2,4-diamino-5-para: bromopheny 1-6-methyl-pyrimidine had a melting point of <B> 262-2650 </B> C.
The same compound was similarly prepared by condensation of guanidine with P-ethoxy-p, -methyl-α-para-bromophenyl-acrylonitrile. After purification, as above, the compound melted. at 262-265 C.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US299944XA | 1950-07-20 | 1950-07-20 | |
| CH297992T | 1951-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH299944A true CH299944A (en) | 1954-06-30 |
Family
ID=25733917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH299944D CH299944A (en) | 1950-07-20 | 1951-06-13 | Process for the preparation of a pyrimidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH299944A (en) |
-
1951
- 1951-06-13 CH CH299944D patent/CH299944A/en unknown
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