GB810846A - New pyrimidine compounds and processes for producing the same - Google Patents
New pyrimidine compounds and processes for producing the sameInfo
- Publication number
- GB810846A GB810846A GB20779/56A GB2077956A GB810846A GB 810846 A GB810846 A GB 810846A GB 20779/56 A GB20779/56 A GB 20779/56A GB 2077956 A GB2077956 A GB 2077956A GB 810846 A GB810846 A GB 810846A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrimidine
- dimethylamino
- methyl
- chlorobenzylmercapto
- chloro
- 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
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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula: <FORM:0810846/IV (b)/1> (wherein R is dimethylamino, diethylamino, methyl-ethyl-amino or a saturated nitrogen containing heterocyclic ring attached to the pyrimidine nucleus through the nitrogen atom, R1 is hydrogen or an alkyl radical, R2 is hydrogen, a halogen or an alkyl radical and "Aralkyl" is an aralkyl group which may be substituted in the aryl radical by a halogen atom), their acid-addition salts and their preparation by one of the following methods: (1) reaction of the appropriate 2-halogenopyrimidine with the appropriate aralkyl-mercaptan; (2) condensation of the appropriate isothiourea-aralkyl ether with a b -keto-carboxylic acid ester, halogenation of the resulting 4-hydroxy-pyrimidine and reaction of the 4-halogeno - pyrimidine with the appropriate secondary amine; and (3) reacting the appropriate 2 - mercapto - 4 - tertiary - aminopyrimidine with the appropriate aralkyl halide. In examples: (1) 2-chloro-4-dimethylamino-6-methyl-pyrimidine and benzyl mercaptan are heated together to give 2-benzylmercapto-4-dimethylamino - 6 - methyl - pyrimidine hydrochloride from which the free base is subsequently isolated; (2) and (3) 2-o-chlorobenzylmercapto - 4 - piperidimo - 6 - methyl - pyrimidine hydrochloride, 2 - o - chlorobenzylmercapto - 4 - dimethylamino - pyrimidine hydrochloride and the free base, 2-o-chlorobenzylmercapto - 4 - dimethylamino - 5 - methyl - pyrimidine hydrochloride and the free base, 2-o-chlorobenzylmercapto-4-dimethylamino - 6 - ethyl - pyrimidine hydrochloride and the free base, 2-o-chlorobenzylmercapto-4-dimethylamino - 5 : 6 - dimethyl - pyrimidine hydrochloride and the free base, 2-p-chlorobenzylmercapto - 4 - dimethylamino - 6 - methyl - pyrimidine hydrochloride and the corresponding m-chloro-compound, and 2-o-chlorobenzylmercapto - 4 - dimethylamino - 5 - chloro - 6 - methyl - pyrimidine are prepared similarly; (4) b -phenylethyl-mercaptan and 2-chloro - 4 - dimethylamino - 6 - methyl - pyrimidine are either heated together at 200 DEG C. or reacted together in pyridine in the presence of aqueous sodium hydroxide at below 30 DEG C. with subsequent heating at 60 DEG to 70 DEG C. to give, on working up in each case, 2-b -phenylethyl - mercapto - 4 - dimethylamino - 6 - methyl-pyrimidine; (5) o-chlorobenzyl-isothiourea ether hydrochloride (prepared from o-chlorobenzylchloride and thiourea) and acetoacetic ester are reacted in the presence of sodium in alcohol to give 2 - o - chlorobenzylmercapto - 4 - hydroxy - 6 - methyl - pyrimidine, this with POCl3 gives 2 - o - chlorobenzylmercapto - 4 - chloro - 6 - methyl - pyrimidine and this on heating with dimethylamine in alcohol gives 2 - o - chlorobenzylmercapto - 4 - dimethylamino - 6 - methyl - pyrimidine hydrochloride from which the free base is subsequently isolated; and (6) 2-mercapto-4-dimethylamino-6-methyl-pyrimidine (prepared by boiling the 2-chloro-compound with sodium hydrosulphide in dilute alcohol) is boiled with sodium in alcohol and then mixed with o-chlorobenzylchloride to give, on working up, the final product of (5).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE810846X | 1955-07-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB810846A true GB810846A (en) | 1959-03-25 |
Family
ID=6725970
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20779/56A Expired GB810846A (en) | 1955-07-05 | 1956-07-04 | New pyrimidine compounds and processes for producing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB810846A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013123401A1 (en) * | 2012-02-17 | 2013-08-22 | Abbvie Inc. | Diaminopyrimidines useful as inhibitors of the human respiratory syncytial virus (rsv) |
-
1956
- 1956-07-04 GB GB20779/56A patent/GB810846A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013123401A1 (en) * | 2012-02-17 | 2013-08-22 | Abbvie Inc. | Diaminopyrimidines useful as inhibitors of the human respiratory syncytial virus (rsv) |
JP2015508079A (en) * | 2012-02-17 | 2015-03-16 | アッヴィ・インコーポレイテッド | Diaminopyrimidines useful as inhibitors of human respiratory polynuclear virus (RSV) |
US9447051B2 (en) | 2012-02-17 | 2016-09-20 | Abbvie Inc. | Diaminopyrimidines and uses thereof |
JP2017160244A (en) * | 2012-02-17 | 2017-09-14 | アッヴィ・インコーポレイテッド | Diaminopyrimidines useful as inhibitors of the human respiratory syncytial virus (rsv) |
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