GB666027A - New pyrimidine derivatives - Google Patents
New pyrimidine derivativesInfo
- Publication number
- GB666027A GB666027A GB1976149A GB1976149A GB666027A GB 666027 A GB666027 A GB 666027A GB 1976149 A GB1976149 A GB 1976149A GB 1976149 A GB1976149 A GB 1976149A GB 666027 A GB666027 A GB 666027A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- propyl
- methyl
- ethyl
- dione
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises pyrimidine derivatives possessing anticonvulsant properties and of the general formula <FORM:0666027/IV (b)/1> (wherein R1 represents a monocyclic carbocyclic radical or an alkenyl radical of not more than 3 carbon atoms, R2 represents an alkyl radical or an alkenyl radical of not more than 3 carbon atoms, and R3 represents hydrogen or an alkyl radical of not more than 4 carbon atoms), and their manufacture by reduction (e.g. with hydrogen, either electrolytically or in the presence of a hydrogenation catalyst) of a compound of the formula <FORM:0666027/IV (b)/2> (wherein X represents oxygen or sulphur and Y represents hydrogen or, when X is sulphur, may represent an alkyl radical), or by condensation of a malondiamide derivative of the formula <FORM:0666027/IV (b)/3> with formamide (e.g. by heating the reactants together). In examples: (1) 5-phenyl-5-ethyl-2-thiobarbituric acid is reduced with Raney nickel in alcohol to 5-phenyl-5-ethylhexahydropyrimidine-4:6-dione; (2) the same product is obtained by refluxing a -phenyl-a -ethylmalondiamide with formamide; (3) 2-methylthio-5-phenyl - 5 - ethyltetrahydropyrimidine - 4:6 - dione is reduced as in (1); (4) 5-phenyl-5-ethylbarbituric acid is reduced electrolytically; (5) the malondiamide in (2) is replaced by the appropriate starting materials to yield 5-phenyl-5-methyl-, -n-propyl- and -allyl- and 5-cyclohexyl - 5 - n - propyl - hexahydropyrimidine - 4:6-dione; (6) the appropriate 5-disubstituted-2-thiobarbituric acids are reduced as in (1) to 5 - phenyl - 5 - isopropyl - and 5 - cyclohexyl - 5-ethyl- and -n-propyl-hexahydropyrimidine-4:6-diones; (7) the malondiamide in (2) is replaced by the appropriate a :a :N-trisubstituted malondiamides to produce 5-phenyl-1:5-diethyl- and -dimethyl-, 5-phenyl-5-methyl-1-n-propyl-, 5-phenyl-5-ethyl-1-methyl- and -n-propyl- and 5-phenyl-5-n-propyl-1-methylhexahydropyrimidine-4:6-dione; (8) a : a -diallylmalondiamide similarly gives 5:5-diallylhexahydropyrimidine-4:6-dione. 2 - Methylthio - 5 - phenyl - 5 - ethyltetrahydro pyrimidine-4:6-dione is obtainable by treating 5 - phenyl - 5 - ethyl - 2 - thiobarbituric acid with methyl iodide in aqueous alcoholic sodium hydroxide. 5 - Phenyl - 5 - methyl- and - isopropyl- and 5 - cyclohexyl - 5 - ethyl - and - n - propyl - 2 - thiobarbituric acids are obtainable by condensing the appropriately substituted malonic esters with thiourea. a - Phenyl - a - n - propyl, - isopropyl - and -allyl- and a -cyclohexyl-a -n-propyl-malondiamides are obtainable by hydrolysing the corresponding malonic esters with aqueous alcoholic sodium hydroxide, treating the free acids with phosphorus pentachloride, and reacting the resulting malonyl chlorides with aqueous ammonia. a - Phenyl - a - methyl - N - methyl - and - n - propyl -, a - phenyl - a - ethyl - N - methyl -, -ethyl- and -n-propyl- and a -phenyl-a -n-propyl-N-methyl-malondiamides are obtainable from the corresponding a :a -disubstituted ethyl cyanacetates by the action of aqueous alcoholic amines to a :a -phenylalkyl-N-alkylcyanacetamides, followed by hydrolysis with cold concentrated sulphuric acid.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1976149A GB666027A (en) | 1949-07-27 | 1949-07-27 | New pyrimidine derivatives |
MY5500017A MY5500017A (en) | 1949-07-27 | 1955-12-31 | Folding chair |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1976149A GB666027A (en) | 1949-07-27 | 1949-07-27 | New pyrimidine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB666027A true GB666027A (en) | 1952-02-06 |
Family
ID=10134772
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1976149A Expired GB666027A (en) | 1949-07-27 | 1949-07-27 | New pyrimidine derivatives |
Country Status (2)
Country | Link |
---|---|
GB (1) | GB666027A (en) |
MY (1) | MY5500017A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1147950B (en) * | 1959-12-21 | 1963-05-02 | Ici Ltd | Process for the preparation of hexahydropyrimidine-4, 6-dione derivatives |
-
1949
- 1949-07-27 GB GB1976149A patent/GB666027A/en not_active Expired
-
1955
- 1955-12-31 MY MY5500017A patent/MY5500017A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1147950B (en) * | 1959-12-21 | 1963-05-02 | Ici Ltd | Process for the preparation of hexahydropyrimidine-4, 6-dione derivatives |
Also Published As
Publication number | Publication date |
---|---|
MY5500017A (en) | 1955-12-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB666027A (en) | New pyrimidine derivatives | |
US3417136A (en) | Aminocarboxylic acids and salts thereof | |
US3742014A (en) | Preparation of benzonitriles | |
US2473042A (en) | 3,5-dihydroxy-4-dihydro-thiadiazine-1-dioxide and its preparation | |
GB741667A (en) | New pyrimidine derivatives | |
US2375735A (en) | Preparation of pyrimidines | |
US2351667A (en) | Production of succinic acids | |
KR970006287A (en) | Improved method of preparing barbituric acid | |
JPH0549666B2 (en) | ||
GB787061A (en) | Process for producing n-methyl--a-phenylsuccinimide | |
GB1180208A (en) | 5-Nitrofuran Derivatives | |
Higginbotham et al. | X.—The formation of substituted succinic acids from esters of α β-unsaturated acids | |
GB775370A (en) | New pyrimidine derivatives and processes for their preparation | |
GB679677A (en) | Improvements in or relating to pyrazolidones | |
US3168538A (en) | Amide sulfonate surface active agents | |
US2269652A (en) | Method for the preparation of isocytosine | |
GB1014157A (en) | Unsaturated amides containing sulphone groups and process for the production thereof | |
KR790001785B1 (en) | Process for preparing 5-benzyl picolic acids | |
DE889151C (en) | Process for the preparation of 2,4-diamino-5-phenyl-pyrimidine-Abkoemmlingen | |
GB720198A (en) | Manufacture of new dioxopiperidines | |
GB734801A (en) | Improvements in and relating to derivatives of pyrimidine and the manufacture thereof | |
GB598309A (en) | Improvements in the production of organic compounds | |
US2336210A (en) | 4-4' derivatives of 2-carboxydiphenylsulphones and esters | |
GB1199613A (en) | Process for Producing 2-Amino-4-Substituted Butyric Acids and their Corresponding Nitriles | |
GB949955A (en) | New lactams and their use in the production of ª -amino-ª -caprolactam |