GB587548A - New pyrimidine compounds - Google Patents

New pyrimidine compounds

Info

Publication number
GB587548A
GB587548A GB1418244A GB1418244A GB587548A GB 587548 A GB587548 A GB 587548A GB 1418244 A GB1418244 A GB 1418244A GB 1418244 A GB1418244 A GB 1418244A GB 587548 A GB587548 A GB 587548A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
group
diethylamino
methylpyrimidine
obtainable
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
GB1418244A
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 GB1418244A priority Critical patent/GB587548A/en
Publication of GB587548A publication Critical patent/GB587548A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic 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
    • C07D239/28Heterocyclic 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
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Pyrimidine compounds of the general formula <FORM:0587548/IV/1> wherein X represents hydrogen or a hydrocarbon radical, Y represents hydrogen or a neutral substituent such as a hydrocarbon radical or an alkoxy, aryloxy, alkylmercapto or cyano group, and also X and Y may be joined together to form an alkylene chain, and of Z and Z1 one represents a hydroxy group and the other a substituted amino group 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 aliphaticcarbocyclic linking group, which may be substituted by hydrocarbon radicals, hydroxy, alkoxy or dialkylaminoalkyl groups, and which, when wholly or partly an aliphatic chain, may be interrupted by oxygen, nitrogen or sulphur atoms, and NRR1 represents an amino or substituted amino group such as alkylamino or dialkylamino or piperidino or other strongly basic nitrogen-containing heterocyclic group, are manufactured by the interaction of a diamine NHR11-A-NRR1 with a 2- or 4-hydroxypyrimidine bearing the atoms or groups Y and X in the 5- and 6-positions respectively and in the 4- or 2-position an alkylmercapto or substituted alkylmercapto group. Alternatively, when NRR1 is a primary amino group, this is protected by acylation and the acyl group is split off after condensation with the pyrimidine compound. The reaction is effected by heating the reagents together, optionally in the presence of a solvent or diluent, e.g. b -ethoxyethanol. When the diamine is of the form NH2-A-NH2 it is preferably used in excess to suppress the side reaction wherein 1 mol. of the diamine combines with 2 mols. of the pyrimidine derivative. The products form salts with mineral and organic acids, e.g. hydrochloric, picric and 3 : 5-dinitrobenzoic acid. When the terminal amino group NRR1 is a primary amino group it can be alkylated or converted to a heterocyclic ring such as a piperidino radicle, e.g. by heating with an alkyl iodide, dimethyl sulphate or pentamethylene dibromide. Examples describe the preparation, from the appropriate diamines and the appropriate 2- or 4-hydroxy-4- or 2-methylmercaptopyrimidines of: 2-b -diethylaminoethylamino-, 2-g -diethyl-, -dimethyl- and -dibutyl-aminopropylamino-, 2 - d - diethylaminobutylamino-, 2 - g - piperidinopropylamino-, 2 - d - diethylamino - a - methylbutylamino-, 2 - g - butylaminopropylamino-, 2 - g - (b 1 - diethylaminoethoxy) - propylamino-, 2 - g - (N - methyl - N - b 1 - diethylaminoethyl)-aminopropylamino-, 2-(N-methyl-N - b - diethylaminoethyl)-amino-, 2-(61-aminohexylamino)- and 2 - b - aminoethylamino - 4 - hydroxy - 6 - methylpyrimidine; 2 - g - diethyl- and -dibutyl-aminopropylamino-4-hydroxy-5-ethyl-6-methylpyrimidine; 4-b -diethylaminoethylamino-, 4 - g - diethylaminopropylamino and 4 - d - diethylamino - a - methylbutylamino-2 - hydroxy - 6 - methylpyrimidine; 2-g -dibutylaminopropylamino- and 2-b -diethylaminoethyl amino - 4 - hydroxy - 5 : 6 - dimethylpyrimidine; and 2-g -dibutylaminopropylamino-4-hydroxypyrimidine. In a further example, 2-methylmercapto - 4 - hydroxy - 6 - methylpyrimidine is heated with monoacetylethylenediamine to produce 2-b -acetylaminoethylamino-4-hydroxy-6-methylpyrimidine, and the acetyl group is then removed by heating with dilute hydrochloric acid. Additional starting materials specified are, on the one hand, 2-dimethylaminoethylamine, 4-dimethyl- and -di-n-butyl-aminobutylamine, 5-dimethyl- and-diethyl-amino-n-amylamine, 3-diethylamino-1 : 2-dimethylpropylamine, 6 - dimethylaminohexylamine, 3 - diethylamino-2-hydroxypropylamine, 2-methylaminoethylamine, 3 - (b - diethylaminoethylmercapto) - propylamine, 2 - pyrrolidinoethylamine, 1 : 3-bis-diethylamino-2-aminopropane, 2-piperidinoethylamine, 2-piperidino-2-methylethylamine, b -piperidino-iso-propylamine, p-diethylaminoethoxyaniline, p - diethylaminoethylmercaptoaniline and 3-diethylamino-2 : 2-dimethylpropylamine, and, on the other hand, 2-ethyl- and -benzyl-mercapto-4-hydroxy-6-methylpyrimidine, 2 - methylmercapto - 4 - hydroxy - 6 - ethyl- and - 6 - phenyl - pyrimidine, 2 - ethylmercapto - 4 - hydroxy - 5 - phenyl-, -5-methyl- and -5-phenoxy-pyrimidine, 2-ethylmercapto-4-hydroxy-5-benzyl-6-methylpyrimidine, 2-methylmercapto-4-hydroxy-5 : 6 : 7 : 8-tetrahydroquinazoline and 2-methylmercapto-4-hydroxy-5 : 6-trimethylenepyrimidine. Specification 587,550 is referred to. 2 - Alkylmercapto - 4 - hydroxypyrimidines are obtainable by interaction of appropriate alkyl isothioureas with formylacetic esters appropriately substituted, where necessary, on the a - and b -carbon atoms, or by direct S-alkylation of the 2 - mercapto - 4 - hydroxypyrimidines obtained from thiourea and formylacetic esters. 2 - Hydroxy - 4 - alkylmercaptopyrimidines are obtainable from the above-mentioned isomers by treatment with phosphorus oxychloride to convert the 4-hydroxy group to chlorine, replacement of this by a mercapto group by the action of sodium or potassium hydrosulphide, acid hydrolysis of the 2-alkylmercapto group and S-alkylation of the resulting 2-hydroxy-4-mercapto compound. 4-Di-n-butylaminobutylamine is obtainable by sodium and ethanol reduction of 4-di-n-butylaminobutyronitrile, which may be made by interaction of 4 - bromobutyronitrile with dibutylamine. 3 - Diethylamino - 1 : 2 - dimethylpropylamine is obtainable by reduction of the oxime of 4-diethylamino-3-methylbutan-2-one, which may be made by condensation of methyl ethyl ketone, formaldehyde and diethylamine. 2-Piperidino-2-methylethylamine is obtainable by reduction of a -piperidinopropionitrile, which may be made by the action of sodium cyanide on the condensation product of piperidine with acetaldehyde-sodium bisulphite. N - Methyl - N - b - diethylaminoethylpropylenediamine is obtainable by reduction of the condensation product of acrylonitrile with b -diethylaminoethylmethylamine.
GB1418244A 1944-09-25 1944-09-25 New pyrimidine compounds Expired GB587548A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1418244A GB587548A (en) 1944-09-25 1944-09-25 New pyrimidine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1418244A GB587548A (en) 1944-09-25 1944-09-25 New pyrimidine compounds

Publications (1)

Publication Number Publication Date
GB587548A true GB587548A (en) 1947-04-29

Family

ID=10036494

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1418244A Expired GB587548A (en) 1944-09-25 1944-09-25 New pyrimidine compounds

Country Status (1)

Country Link
GB (1) GB587548A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3178432A (en) * 1957-12-06 1965-04-13 Ciba Geigy Corp New 2-substituted pyrimidines
US3980781A (en) 1966-03-31 1976-09-14 Imperial Chemical Industries Limited Fungicidal composition and method containing 2-amino-pyrimidines
US20210309616A1 (en) * 2017-03-22 2021-10-07 The Research Foundation For The State University Of New York Substituted quinazolines as matrix metalloproteinase-9 hemopexin domain inhibitors

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3178432A (en) * 1957-12-06 1965-04-13 Ciba Geigy Corp New 2-substituted pyrimidines
US3980781A (en) 1966-03-31 1976-09-14 Imperial Chemical Industries Limited Fungicidal composition and method containing 2-amino-pyrimidines
US20210309616A1 (en) * 2017-03-22 2021-10-07 The Research Foundation For The State University Of New York Substituted quinazolines as matrix metalloproteinase-9 hemopexin domain inhibitors
US12018003B2 (en) * 2017-03-22 2024-06-25 The Research Foundation For The State University Of New York Substituted pyrimidines as matrix metalloproteinase-9 hemopexin domain inhibitors

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