GB583815A - New pyrimidine compounds - Google Patents

New pyrimidine compounds

Info

Publication number
GB583815A
GB583815A GB93944A GB93944A GB583815A GB 583815 A GB583815 A GB 583815A GB 93944 A GB93944 A GB 93944A GB 93944 A GB93944 A GB 93944A GB 583815 A GB583815 A GB 583815A
Authority
GB
United Kingdom
Prior art keywords
amino
group
chloro
hydroxy
diethylamino
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
GB93944A
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.)
BARBARA JEAN LOVELL
LAURENCE CONRAD PAYMAN
Imperial Chemical Industries Ltd
Original Assignee
BARBARA JEAN LOVELL
LAURENCE CONRAD PAYMAN
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 BARBARA JEAN LOVELL, LAURENCE CONRAD PAYMAN, Imperial Chemical Industries Ltd filed Critical BARBARA JEAN LOVELL
Priority to GB93944A priority Critical patent/GB583815A/en
Publication of GB583815A publication Critical patent/GB583815A/en
Expired legal-status Critical Current

Links

Abstract

Pyrimidine compounds, useful as chemotherapeutic agents, of the general formula <FORM:0583815/IV/1> wherein X and Y represent hydrogen or hydrocarbon radicals or jointly an alkylene chain, R11 represents hydrogen or an alkyl or simply substituted alkyl (e.g. alkoxyalkyl or dialkylaminoalkyl) group, A represents an aliphatic, alicyclic or aliphatic-carbocyclic linking group, which may be substituted (e.g. by hydrocarbon radicals or hydroxy, alkoxy 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 strongly basic amino or substituted amino group (e.g. 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 an appropriate 2-aminopyrimidine bearing the atoms or groups Y and X in the 5- and 6-positions and a halide group, such as a halogen atom or a hydrocarbon radical which is attached by means of an ether or thioether linkage (e.g. an alkoxy, aryloxy or alkylmercapto group), in the 4-position. Alternatively, such a pyrimidine derivative is reacted with an amino compound of the form NHR11-A1-B, wherein A1 represents either the whole or part of the group A above and B represents a reactive group which is then converted directly or indirectly, by methods involving the step of reaction with ammonia or a compound containing an amino group, into the amino group NRR1 or into a group A11-NRR1 such that A1 and A11 together constitute the group A above. Thus the group B may be a hydroxy group or a derivative thereof which is, or is readily convertible to, a reactive ester thereof (e.g. a halide), which is then reacted with an amine, an amino-substituted amine or a hydroxy- or mercapto-substituted amine. Alternatively, when R1 is hydrogen, the diamine is replaced by its acyl derivative NHR11-A-NR-acyl, and the acyl group is subsequently hydrolysed off. The terminal amino group, when unsubstituted, may be subsequently modified by alkylation, conversion to a heterocyclic group, or reaction with a halogen-substituted amine Hal-A111-NRR1 so as to extend the linking group A to A-NH-A111. The reactions are effected by heating the reagents together, optionally in the presence of a solvent or diluent. Either of the reagents may be used in the form of a salt (e.g. hydrochloride or acetate), and, if desired, an acid-binding agent such as sodium hydroxide may be present. The products form salts with mineral or organic acids such as hydrogen halides and sulphuric, phosphoric, acetic, lactic, tartaric, lower alkanesulphonic (e.g. methanesulphonic), picric, 3 : 5-dinitrobenzoic, methylene bis-2 : 3-hydroxy-naphthoic and methylene bis-salicylic acids. In examples, pyrimidine derivatives of the general formula given above are made from: 2-amino-4-chloro-5 : 6-dimethylpyrimidine and b -diethyl-or dimethyl-aminoethylamine, g -diethyl-, dimethyl- or di-n-butyl-aminopropylamine, d -diethylaminobutylamine, d - diethylamino - a - methylbutylamine, g - n - butylaminopropyl - amine, g -piperidinopropylamine, g -(N-methyl-N - b 1 - diethylaminoethyl) - aminopropylamine, g -(b 1-diethylaminoethoxy)-propylamine, ethylene diamine or b -diethylaminoethylmethylamine; 2-amino-4 - chloro - 5 - ethyl - 6 - methylpyrimidine and d -diethylamino-a -methylbutylamine or b -diethylaminoethylamine; 2-amino-4 - chloro - 6 - methylpyrimidine and b - diethylaminoethylamine or d -diethylamino-a -methylbutylamine; 2 - amino - 4 - chloro - 5 - benzyl - 6 - methylpyrimidine and b - diethylaminoethyl - amine, g - diethylaminopropylamine or d - di - ethylamino-a -methylbutylamine; 2-amino-4-chloro - 5 : 6 - tri- or tetramethylenepyrimidine and the same three diamines; and from 2 - amino - 4 - chloro - 5 - methylpyrimidine and b -diethylaminoethylamine or g -diethylaminopropylamine. In a further example, a solution of 2 - amino - 4 - b - aminoethylamino - 5 : 6 - dimethylpyrimidine and n-butyraldehyde in alcohol is shaken with hydrogen in the presence of a palladium-barium sulphate catalyst to produce 2-amino-4-b -n-butylaminoethylamino-5 : 6-dimethylpyrimidine. Additional starting materials specified are, on the one hand, 2-amino-4-chloropyrimidine and the 4-bromo-, 4-ethoxy-, 4-phenoxy- and 4-methylmercapto-compounds corresponding to this starting material and to those of the examples; and, on the other hand, 3 - diethylamino - 1 : 2 - dimethylpropylamine, 3 - diethylamino - 2 - hydroxypropylamine, 2 - methylaminoethyl - amine, 3 - (b -diethylaminoethylmercapto) - propylamine, 5 - diethylamino - 1 - aminopentane, 2 - pyrrolidinoethylamine, 1 : 3 - bis - diethyl - amino-2-aminopropane, N-ethyl-N-b -diethylaminoethylethylenediamine, 2 - piperidinoethylamine, p-diethylaminoethoxyaniline, p-diethylaminoethylmercaptoaniline, 3 - diethylamino - 2 : 2 - dimethylpropylamine, b - piperidino - b - methylethylamine, N-methyl- and N-ethyl-N1-diethylethylenediamine and bis - (b - diethyl - aminoethyl)-amine. According to the second Provisional Specification, the substituent Y in the 5-position may be any neutral substituent. 2-Aminopyrimidines containing ether or thioether groups in the 4-position, are obtainable by interaction of the corresponding 4-halogenoderivatives with the appropriate hydroxy or mercapto compounds or alkali metal derivatives thereof. 2-Amino-4-chloro-5-benzyl-6-methylpyrimidine is obtained by refluxing phosphorus pentachloride with the corresponding 4-hydroxy-compound, which may be made by interaction of guanidine hydrochloride with ethyl a -benzylacetoacetate in the presence of sodium ethoxide. 2-Amino-4-chloro-5 : 6-tetramethylenepyrimidine is obtainable by the action of phosphorus oxychloride on the corresponding 4-hydroxy-compound. 2-Amino-4-chloro-5 : 6-trimethylenepyrimidine may be similarly prepared from the corresponding 4-hydroxy-compound obtainable by interaction of guanidine hydrochloride with ethyl cyclopentanone-2-carboxylate in the presence of sodium ethoxide. 2-Amino-4-chloro-5-methylpyrimidine is obtainable similarly from the 4 - hydroxy - compound made by interaction of guanidine hydrochloride with sodium a -formylpropionic ester (obtained from ethyl formate, ethyl propionate and sodium).
GB93944A 1944-05-18 1944-05-18 New pyrimidine compounds Expired GB583815A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB93944A GB583815A (en) 1944-05-18 1944-05-18 New pyrimidine compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB93944A GB583815A (en) 1944-05-18 1944-05-18 New pyrimidine compounds

Publications (1)

Publication Number Publication Date
GB583815A true GB583815A (en) 1946-12-31

Family

ID=9713156

Family Applications (1)

Application Number Title Priority Date Filing Date
GB93944A Expired GB583815A (en) 1944-05-18 1944-05-18 New pyrimidine compounds

Country Status (1)

Country Link
GB (1) GB583815A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1082267B (en) * 1951-11-06 1960-05-25 Rhone Poulenc Sa Process for the preparation of new derivatives of pyrimidine
US3178432A (en) * 1957-12-06 1965-04-13 Ciba Geigy Corp New 2-substituted pyrimidines
US3185691A (en) * 1965-05-25 Gycloocteno-pyrimroines
US3299068A (en) * 1966-02-10 1967-01-17 Searle & Co 2, 4-diamino-5, 6, 7, 8-tetrahydro-6-phenylquinazoline and congeners
EP1437348A1 (en) * 2003-01-13 2004-07-14 L'oreal 6-methyl-2,4-diamino-pyrimidine derivatives, process for preparation, compositions containing them and their uses as basic neutralising agents
WO2006016014A1 (en) * 2004-07-13 2006-02-16 L'oreal Novel compounds of a 6-methyl-pyrimidine-2,4-diamine family, method for synthesising, compositions containing said compounds and the use thereof
US8415366B2 (en) 2007-02-14 2013-04-09 Janssen Pharmaceutica Nv 2-aminopyrimidine modulators of the histamine H4 receptor

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3185691A (en) * 1965-05-25 Gycloocteno-pyrimroines
DE1082267B (en) * 1951-11-06 1960-05-25 Rhone Poulenc Sa Process for the preparation of new derivatives of pyrimidine
US3178432A (en) * 1957-12-06 1965-04-13 Ciba Geigy Corp New 2-substituted pyrimidines
US3299068A (en) * 1966-02-10 1967-01-17 Searle & Co 2, 4-diamino-5, 6, 7, 8-tetrahydro-6-phenylquinazoline and congeners
EP1437348A1 (en) * 2003-01-13 2004-07-14 L'oreal 6-methyl-2,4-diamino-pyrimidine derivatives, process for preparation, compositions containing them and their uses as basic neutralising agents
WO2006016014A1 (en) * 2004-07-13 2006-02-16 L'oreal Novel compounds of a 6-methyl-pyrimidine-2,4-diamine family, method for synthesising, compositions containing said compounds and the use thereof
US8415366B2 (en) 2007-02-14 2013-04-09 Janssen Pharmaceutica Nv 2-aminopyrimidine modulators of the histamine H4 receptor
US8686142B2 (en) 2007-02-14 2014-04-01 Janssen Pharmaceutica Nv 2-aminopyrimidine modulators of the histamine H4 receptor
US8716475B2 (en) 2007-02-14 2014-05-06 Janssen Pharmaceutica Nv 2-aminopyrimidine modulators of the histamine H4 receptor

Similar Documents

Publication Publication Date Title
US3272811A (en) Dihydrothieno-[3, 4-d]-pyrimidines
DK150142B (en) METHOD OF ANALOGUE FOR THE PREPARATION OF 5- (2-IMIDAZOLIN-2-YL) -AMINOPYRIMIDINES OR ACID ADDITION SALTS.
US2407966A (en) Diazine compounds
GB583815A (en) New pyrimidine compounds
GB937726A (en) New 4-mercapto-pyrazolo[3,4-d]pyrimidines and process for preparing same
US3178432A (en) New 2-substituted pyrimidines
DE3277373D1 (en) Process for preparing substituted pyrimidinones and intermediates therefor
KR840004076A (en) Method for preparing thiomethyl parridine derivative
US2422887A (en) Pyrimidine compound and processes
US2433440A (en) Jpyrimidine cosipounds
GB1342024A (en) Triazine herbicides
GB581334A (en) New pyrimidine compounds
GB587548A (en) New pyrimidine compounds
US3900476A (en) 2(2&#39;-pyrimidylamino)quinazolines and their preparation
GB590706A (en) New pyrimidine compounds
US3758472A (en) Preparation of-2-alkoxy-4-hydroxypyrimidines
GB587550A (en) New pyrimidine compounds
HU184816B (en) Process for producing substituted imidazolyl-methyl-thio-pyrami done derivatives
ES8306733A1 (en) Novel aniline derivatives, process for preparing the same and cardiotonic compositions containing the same.
GB1108288A (en) Improvements in or relating to pyrimidine compounds
GB600337A (en) New pyrimidine compounds
GB593499A (en) New pyrimidine compounds
GB869977A (en) Diazacycloalkenes and the preparation thereof
US3591589A (en) 6-dialkylaminoalkoxy - 2-aryl-4-chloropyrimidines and 6-dialkylaminoalkylthio-2-aryl-4-chloropyrimidines
US2676965A (en) Method of preparing 2-mercapto-4-tertiary aminopyrimidines