GB710266A - New pyrimidine derivatives - Google Patents
New pyrimidine derivativesInfo
- Publication number
- GB710266A GB710266A GB802051A GB802051A GB710266A GB 710266 A GB710266 A GB 710266A GB 802051 A GB802051 A GB 802051A GB 802051 A GB802051 A GB 802051A GB 710266 A GB710266 A GB 710266A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- phenyl
- dione
- ethyl
- prepared
- 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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 2-alkoxy-hexahydropyrimidine-4 : 6-dione derivatives and tetrahydropyrimidine-4 : 6-dione derivatives of the respective formul <FORM:0710266/IV (b)/1> <FORM:0710266/IV (b)/2> wherein R1 stands for an aryl radical, R2 stands for an alkyl radical, R3 stands for hydrogen or for an alkyl radical of not more than 4 carbon atoms and R4 stands for an alkyl radical or an aralkyl radical and hydrates and salts of compounds of formula II. The salt may be converted to hydrate by adjusting its aqueous solution to pH 6. The compounds of formula I are prepared by subjecting a 2-thio-barbituric acid of the formula <FORM:0710266/IV (b)/3> or an S-alkyl derivative thereof, to reductive desulphurisation, e.g. by hydrogen-containing finely divided metal catalysts, in the presence of an alcohol of the formula R4OH. Compounds of the formula I wherein R3 stands for hydrogen, may be produced by reacting in the presence of an alcohol of formula R4OH (a) a malondiamide derivative of the formula R1R2C(CONH2)2 with a formic acid ester; (b) a compound of the formula <FORM:0710266/IV (b)/4> with an alkali metal hydroxide; (c) an ester of a malonic acid derivative of the formula R1R2C(COOH)2 with formamidine. Compounds of formula I may also be prepared by reacting the compounds of formula II or their salts or hydrates with an alcohol R4OH. Products of formula II may be prepared by treating compounds of formula I with mineral acids or subliming such compounds in high vacuum. The products have anti convulsant properties. They may be used in the process of Specification 710,267. Raney nickel or cobalt catalysts are suitable. In examples, 2-ethoxy-5-phenyl 5-ethylhexahydropyrimidine - 4 : 6 - dione is prepared by treating 5-phenyl-5-ethyl-2-thiobarbituric acid with ethanol and (1) Raney nickel (W1); (2) Raney cobalt; (4) Raney nickel (W5); replacing the ethanol of (1) by methanol yields the corresponding 2-methoxy compound. In further examples: (3) 2-methoxy-5-phenyl-1-methyl-5-ethyl hexahydropyrimidine-4 : 6-dione and the corresponding 1-ethyl compound are prepared by reacting 5-phenyl-1-methyl - 5 - ethyl - 2 - thiobarbituric acid and the corresponding 1-ethyl compound respectively with methanol and Raney cobalt; (5), (7) and (9) 2-methoxy-5-phenyl-5-ethyl-hexahydropyrimidine - 4 : 6 - dione is prepared by reacting (5) a : a - phenylethylmalondiamide, sodium, methanol and ethyl formate; (7) diethylphenylethylmalonate, sodium methoxide, methanol, and formamidine hydrochloride; (9) N-formyl - a : a - phenylethylmalondiamide, methanol and sodium; (6) and (8) 2-ethoxy-5-phenyl - 5 - methylhexahydropyrimidine - 4 : 6 - dione is prepared by (6) reacting a : a -phenylmethylmalondiamide, ethyl formate, ethanol and sodium; (8) reducing 2-methylthio-5-phenyl-5-ethyl tetrahydropyrimidine-4 : 6-dione with Raney nickel (W1); (10) 5-phenyl-5-ethyletrahydropyrimidine - 4 : 6 - dione monohydrochloride is produced by reacting 2-methoxy - 5 - phenyl - 5 - ethylhexahydropyrimidine-4 : 6-dione in ether with hydrogen chloride gas. The product reacts with alcohols to give the corresponding 2-alkoxy-5-phenyl-5-ethyl hexahydropyrimidine - 4 : 6 - dione, the 2 - n - propoxy-, 2-iso-propoxy-, 2-n-butyloxy-, 2-sec.-butyloxy-, 2-n-amyloxy-, 2-n-octyloxy- and 2-benzyloxy-derivatives being thus prepared; (11) 5 - phenyl - 5 - ethyltetrahydropyrimidine - 4 : 6-dione monohydrate is prepared by adjusting an aqueous solution of the corresponding monohydrochloride to pH 6 and allowing to stand. N-Formyl derivatives of the formula <FORM:0710266/IV (b)/5> may be obtained by oxidation of a methylol derivative of the diamide, e.g. with chromic acid. 5 - Phenyl - 1 - methyl - 5 - ethyl - 2 - thiobarbituric acid is prepared by heating phenylethyl malonyl chloride with N-methyl-thiourea. Specification 666,027 also is referred to.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB802051A GB710266A (en) | 1951-04-06 | 1951-04-06 | New pyrimidine derivatives |
DEI5698A DE922049C (en) | 1951-04-06 | 1952-04-06 | Process for the preparation of 2-alkoxyhexahydropyrimidine-4, 6-dione derivatives or the corresponding tetrahydropyrimidine derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB802051A GB710266A (en) | 1951-04-06 | 1951-04-06 | New pyrimidine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB710266A true GB710266A (en) | 1954-06-09 |
Family
ID=9844249
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB802051A Expired GB710266A (en) | 1951-04-06 | 1951-04-06 | New pyrimidine derivatives |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE922049C (en) |
GB (1) | GB710266A (en) |
-
1951
- 1951-04-06 GB GB802051A patent/GB710266A/en not_active Expired
-
1952
- 1952-04-06 DE DEI5698A patent/DE922049C/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE922049C (en) | 1955-01-07 |
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