GB715813A - Improvements in derivatives of pyrimidine - Google Patents
Improvements in derivatives of pyrimidineInfo
- Publication number
- GB715813A GB715813A GB12724/51A GB1272451A GB715813A GB 715813 A GB715813 A GB 715813A GB 12724/51 A GB12724/51 A GB 12724/51A GB 1272451 A GB1272451 A GB 1272451A GB 715813 A GB715813 A GB 715813A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- chlorophenyl
- phenyl
- ethyl
- radical
- 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
- C07D239/48—Two nitrogen atoms
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
Abstract
The invention comprises compounds, having improved antimalarial properties, of the general formula <FORM:0715813/IV (b)/1> wherein Ar represents a 3- or 4-halophenyl, 3 : 4-dihalophenyl or 4-nitrophenyl radical, R represents a primary alkyl radical of 1-5 carbon atoms and X represents NH2, and their salts, and the manufacture of compounds of the said general formula wherein Ar represents any aryl radical, which may be substituted, R represents hydrogen, or an aryl or alkyl radical either of which may be substituted, and X represents hydrogen or an alkyl or aryl radical, or NH2 when R is other than hydrogen, by condensing a compound (guanidine or an amidine) of the formula X-C(: NH)NH2 with a b -alkoxy-a -arylacrylonitrile of the formula <FORM:0715813/IV (b)/2> (wherein R1 represents an alkyl or aralkyl radical). The latter reactant is preferably prepared in situ from the corresponding b -hydroxy compound (tautomeric with an a -acyl-a -arylacetonitrile). In examples: (1) a -acetyl-p-chlorophenylacetonitrile is treated with diazomethane in ether and the product is refluxed with guanidine in alcohol to produce 2 : 4-diamino - 5 - p - chlorophenyl - 6 - methylpyrimidine; the same compound is obtainable by condensing guanidine with b -ethoxy-b -methyl - a - p - chlorophenylacrylonitrile; (2) a - propionyl - p - chlorophenylacetonitrile is treated as in the first part of (1) to form 2 : 4-diamino - 5 - p - chlorophenyl - 6 - ethylpyrimidine; (3)-(5), (8)-(10) and (13) the corresponding 6 - n - propyl, 6 - isobutyl, 6-a -ethyl-n-propyl, 6-n-amyl, 6-n-undecyl, 6-b -phenethyl and 6-phenyl compounds are similarly prepared; (6) 2 : 4-diamino-5-phenyl - 6-methylpyrimidine is prepared similarly or from b - methyl - b - benzyloxy - a - phenylacrylonitrile; (7) the product of (6) is nitrated in the para-position of the 5-phenyl group; (11), (12) (14), and (24)-(35) by the process of the first part of (1) are prepared 2 : 4-diamino-5-phenyl-6 - (N - methyl - N - phenylaminomethyl)-, -5-a -naphthyl-6-methyl-, -5 : 6-diphenyl-, -5-p-chlorophenyl-6-n-butyl-, -5-p-nitrophenyl-6-ethyl-, -5-p-bromophenyl-6-ethyl-, -5-m-fluorophenyl-6-methyl-, -5-m-chlorophenyl-6-methyl-, - 5 - m - bromophenyl - 6 - methyl -, - 5 - (31 : 41-dichlorophenyl) - 6 - methyl -, - 5 - (31 : 41-dichlorophenyl) - 6 - ethyl -, - 5 - (31 : 41 - dichlorophenyl) - 6 - n - propyl -, - 5 - (31 : 41-dichlorophenyl - 6 - n - butyl -, - 5 - (31 : 41-dibromophenyl) - 6 - ethyl - and - 5 - (31-bromo - 41 - chlorophenyl) - 6 - methyl - pyrimidine; (15)-(23) from the appropriate amidines and b -methoxy-a -arylacrylonitriles are prepared 4-amino-5-phenyl-, -6-methyl-5-phenyl -, - 5 - p - chlorophenyl - 6 - phenyl -, - 2 - methyl - 5 - p - chlorophenyl -, - 5 - p-chlorophenyl - 2 : 6 - dimethyl -, - 5 - p - chlorophenyl - 2 - methyl - 6 - phenyl -, - 5 - p - chlorophenyl - 2 - p - tolyl -, - 5 - p - chlorophenyl - 6-methyl - 2 - phenyl - and - 5 - p - chlorophenyl-6-phenyl-2-p-tolyl-pyrimidine. a - Acyl - a - arylacetonitriles of the general formula <FORM:0715813/IV (b)/3> are obtainable by condensing, in the presence of an alkali metal alkoxide, arylacetonitriles with esters RCOO Alkyl, e.g. p-chlorophenylacetonitrile with ethyl propionate or ethyl benzoate, phenylacetonitrile with N-phenyl-N-methylglycine ester, or m-fluorophenylacetonitrile with ethyl acetate. Arylacetonitriles are obtainable by reacting arylmethyl halides with alkali metal cyanides, e.g. m-fluorotoluene is refluxed with sulphuryl chloride in the presence of benzoyl peroxide and the product is refluxed with potassium cyanide in aqueous ethanol to produce m-fluorophenylacetonitrile.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US715813XA | 1950-06-14 | 1950-06-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB715813A true GB715813A (en) | 1954-09-22 |
Family
ID=22102243
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12724/51A Expired GB715813A (en) | 1950-06-14 | 1951-05-30 | Improvements in derivatives of pyrimidine |
Country Status (2)
Country | Link |
---|---|
CY (1) | CY135A (en) |
GB (1) | GB715813A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5136080A (en) * | 1989-12-04 | 1992-08-04 | Burroughs Wellcome Co. | Nitrile compounds |
US5597828A (en) * | 1988-12-07 | 1997-01-28 | Glaxo Wellcome Inc. | Certain 2,4-diamino-5-(2,3-dihalophenyl)-6-substituted pyrimidines which are pharmacologically active CNS compounds |
-
1951
- 1951-05-30 GB GB12724/51A patent/GB715813A/en not_active Expired
-
1955
- 1955-07-14 CY CY13555A patent/CY135A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5597828A (en) * | 1988-12-07 | 1997-01-28 | Glaxo Wellcome Inc. | Certain 2,4-diamino-5-(2,3-dihalophenyl)-6-substituted pyrimidines which are pharmacologically active CNS compounds |
US5136080A (en) * | 1989-12-04 | 1992-08-04 | Burroughs Wellcome Co. | Nitrile compounds |
Also Published As
Publication number | Publication date |
---|---|
CY135A (en) | 1955-07-14 |
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