GB587550A - New pyrimidine compounds - Google Patents

New pyrimidine compounds

Info

Publication number
GB587550A
GB587550A GB1418444A GB1418444A GB587550A GB 587550 A GB587550 A GB 587550A GB 1418444 A GB1418444 A GB 1418444A GB 1418444 A GB1418444 A GB 1418444A GB 587550 A GB587550 A GB 587550A
Authority
GB
United Kingdom
Prior art keywords
nitro
methylpyrimidine
anilino
methyl
chloroanilino
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
Application number
GB1418444A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
MARGARET ISABEL DAVIS
Imperial Chemical Industries Ltd
Original Assignee
MARGARET ISABEL DAVIS
Imperial Chemical Industries Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by MARGARET ISABEL DAVIS, Imperial Chemical Industries Ltd filed Critical MARGARET ISABEL DAVIS
Priority to GB1418444A priority Critical patent/GB587550A/en
Publication of GB587550A publication Critical patent/GB587550A/en
Expired legal-status Critical Current

Links

Abstract

Pyrimidine compounds, useful as chemotherapeutic agents and as intermediates therefor, of the general formula <FORM:0587550/IV/1> wherein X represents hydrogen or a hydrocarbon radicle, Y represents hydrogen or a neutral substituent such as a hydrocarbon radical or an alkoxy, aryloxy, alkylmercapto, cyano or nitro group, and also X and Y may be joined together to form an alkylene chain, and of Z and Z1 one represents an arylamino group, free from strongly acidic substituents (such as sulphonic, carboxylic, phosphoric, or arsonic acid or sulphuric ester groups) but optionally bearing one or more other nuclear substituents, e.g. feebly acidic groups such as phenolic hydroxy or mercapto groups, halogen atoms, nitro, cyano or esterified carboxyl groups or hydrocarbon radicals (which themselves may bear substituents and which may be attached to the acrylamino group directly or through an oxygen, nitrogen or sulphur atom or a carboxyl group), and the other represents a radical of the form -NR11-A-NRR1 wherein R11 represents hydrogen or an alkyl or substituted alkyl (e.g. alkoxyalkyl or dialkylaminoalkyl) group, A represents an aliphatic, alicyclic or aliphatic-carbocyclic linking group which may be substituted by hydrocarbon radicals, alkoxy groups or dialkylaminoalkyl groups, and which, when wholly or partly an aliphatic chain, may be interrupted by oxygen, sulphur or nitrogen atoms, and -NRR1 represents a substituted amino group such as alkylamino or dialkylamino, or piperidino or other strongly basic nitrogen-containing heterocyclic group, are manufactured by the interaction of an appropriate primary arylamine with an appropriate pyrimidine derivative bearing in the 2- or 4-position the group -NR11-A-NRR1, in the 5- and 6-position the atoms or groups Y and X respectively and in the 4- or 2-position a halogen atom. The reaction may be affected by heating together the reagents, either of which may be in the form of a salt (e.g. the hydrochloride or acetate), optionally in the presence of a solvent or diluent (which may be an excess of the arylamine), or conveniently in an aqueous medium using one molecular proportion of each of the reagents and one or slightly more than one of a mineral acid. The products form salts with mineral and organic acids, e.g. hydrogen halides, sulphuric, phosphoric, picric, acetic, lactic, tartaric, lower alkanesulphonic (e.g. methanesulphonic), methylene bis-2 : 3-hydroxynaphthoic and methylene bis-salicylic acids. Examples describe the preparation, from the appropriate arylamines (or salts thereof) and the appropriate 2- or 4-chloropyrimidines (or salts thereof), of: 2-g -diethyl-, -dimethyl- or -dibutyl-aminopropylamino-, 2-b -diethylaminoethylamino-, 2 - d - diethylaminobutylamino-, 2 - g - piperidinopropylamino-2 - g - butylaminopropylamino-, 2 - (N - methyl-N - b - diethylaminoethyl) - amino -, 2 - d - diethylamino - a - methylbutylamino-, 2 - g - (b 1-diethylaminoethoxy) - propylamino - and 2 - g -(N - methyl - N - b 1 - diethylaminoethylamino)-propylamino - 4 - p - chloroanilino - 6 - methyl-pyrimidine; 4-anilino-, 4-p-methyl-, methoxy-, -nitro- and -cyano-anilino-, 4-(31 : 41-dichloroanilino)- and 4-(61-bromo-21-naphthylamino)-2 - b - diethylaminoethylamino - 6 - methyl-pyrimidine; 2-g -diethyl- and -dibutyl-amino propylamino - 4 - p - chloroanilino - 5 - ethyl - 6 - methylpyrimidine; 2-anilino-, 2-p-chlor-methoxy-, -methyl-, -methylmercapto-, hydroxy, and -ethoxy - anilino-, 2 - o - chloro-, -methoxy- and -methyl - anilino-, 2 - m - methyl-and -nitro-anilino-, 2-a - and -b -naphthylamino-, 2 - (61 - bromo- and -methoxy - 21 - naphthyl)-amino- and 2 - (41 - chloro - 11 - naphthyl)-amino - 4 - b - diethylaminoethylamino - 6 - methylpyrimidine; 2-g -diethyl- and -dibutyl aminopropylamino-, (2 - g - mono - n - butyl-aminopropylamino-, 2 - g - piperidinopropylamino- and 2 - d - diethylamino - a - methyl-butylamino - 4 - (61 - bromo - 21 - naphthyl) - amino - 6 - methylpyrimidine; 4 - p - bromo -, -cyano-, -hydroxy- and -nitro-anilino-, 4-(21 : 41- and 31 : 41-dichloroanilino)- an 4-m-chloroanilino - 2 - g - dibutylaminopropylamino-6-methylpyrimidine; 4-m- and p-nitro anilino- and 4-p-cyanoanilino-2-g -piperidinopropylamino-6-methylpyrimidine; 4-p-cyano-hydroxy- and -nitro - anilino - 2 - g - diethyl-aminopropylamino - 4 - methylpyrimidine; 2-p-chloro-, -dimethylamino-, -bromo-, butyl-, -carbomethoxy-, -phenyl-, -nitro- and -cyanoanilino-, 2-o- and m-chloroanilino-, 2-(21 : 41-, 31-41, 31-41- and 21 : 51-dichloroanilino)-, 2-(21-methyl - 41 - chloroanilino)-, 2 - (31 - chloro - 41 - methylanilino)-, 2-(31 : 41- and 31 : 51-dimethylanilino)- 2-(31 : 51 - dibromoanilino)-, 2 - b - naphthylamino- and 2 - (61 - bromo - 21 - naphthylamino) - 4 - g - diethylaminopropylamino - 6 - methylpyrimidine; 2 - p - chloroanilino - 4 - g - diethylaminopropylaminopyrimidine; 2 - o -, m- and p-chloroanilino-, 2-o- and p-methoxyanilino-, 2-p-bromoanilino- and 2-(33 : 41-dichloroanilino) - 4 - d - diethylamino - a - methyl-butylamino - 6 - methylpyrimidine; 4 - p cyano- and -nitro - anilino - 2 - d - diethylamino - a - methylbutylamino - 6 - methylpyrimidine; 4-p-nitro- and -cyano-anilino-2-g -diethylaminopropylamino - 5 - ethyl - 6 - methylpyrimidine; 2 - g - dibutylaminopropylamino - 4 - p - nitro- and -chloro - anilinopyrimidine; 2-g -(b 1-diethylaminoethoxy)-propylamino-, 2 - g - butylaminopropylamino- and 2 - g - dimethylaminopropylamino - 4 - p - nitro-anilino - 6 - methylpyrimidine; 4 - g - diethylaminopropylamino- and 4 - b - diethylaminoethylamino - 2 - p - chloroanilino - 5 - nitro - 6 - methylpyrimidine. Additional arylamines specified are o-bromoaniline, p-mercaptoaniline, p-dimethylaminosulphonylaniline and 6-hydroxy-2-naphthylamine. 4 - g - Diethylaminopropylamino- and 4 - b - diethylaminoethylamino - 2 - chloro - 5 - nitro - 6 - methylpyrimidine hydrochlorides, which are the starting materials for the last two products named above, are obtainable by the interaction of 2 : 4-dichloro-5-nitro-6-methylpyrimidine in ethanol with an equimolecular proportion of g -diethylaminopropylamine and b -diethylaminoethylamine respectively. Specifications 584,917, 587,548 and 587,549 are referred to.
GB1418444A 1944-09-25 1944-09-25 New pyrimidine compounds Expired GB587550A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1418444A GB587550A (en) 1944-09-25 1944-09-25 New pyrimidine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1418444A GB587550A (en) 1944-09-25 1944-09-25 New pyrimidine compounds

Publications (1)

Publication Number Publication Date
GB587550A true GB587550A (en) 1947-04-29

Family

ID=10036531

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1418444A Expired GB587550A (en) 1944-09-25 1944-09-25 New pyrimidine compounds

Country Status (1)

Country Link
GB (1) GB587550A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1009632B (en) * 1954-06-08 1957-06-06 Cassella Farbwerke Mainkur Ag Process for the preparation of cytotoxic compounds
US3178432A (en) * 1957-12-06 1965-04-13 Ciba Geigy Corp New 2-substituted pyrimidines
JP2003510327A (en) * 1999-09-30 2003-03-18 ニューロジェン・コーポレーション Heterocycle substituted with specific alkylenediamine
US8158641B2 (en) 2006-06-15 2012-04-17 Boehringer Ingelheim International Gmbh 2-anilino-4-aminoalkyleneaminopyrimidines
US8354407B2 (en) 2006-06-15 2013-01-15 Boehringer Ingelheim International Gmbh 2-anilino-4-(heterocyclic)amino-pyrimidines

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1009632B (en) * 1954-06-08 1957-06-06 Cassella Farbwerke Mainkur Ag Process for the preparation of cytotoxic compounds
US3178432A (en) * 1957-12-06 1965-04-13 Ciba Geigy Corp New 2-substituted pyrimidines
JP2003510327A (en) * 1999-09-30 2003-03-18 ニューロジェン・コーポレーション Heterocycle substituted with specific alkylenediamine
US8158641B2 (en) 2006-06-15 2012-04-17 Boehringer Ingelheim International Gmbh 2-anilino-4-aminoalkyleneaminopyrimidines
US8354407B2 (en) 2006-06-15 2013-01-15 Boehringer Ingelheim International Gmbh 2-anilino-4-(heterocyclic)amino-pyrimidines

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