Patent GB-763043-A (GB)
Title: New pyrimidine derivatives
Inventor: BOON WILLIAM ROBERT
IPC: C09B43/40
Filed: 1952-04-18
Abstract: The invention comprises pyrimidine compounds of the general formula <FORM:0763043/IV(b)/1> in which X and Y are lower alkyl radicals of not more than 6 carbon atoms; B is hydroxyl, amino or a substituted amino group; Ar is an aryl radical which may bear substituents; R is hydrogen; R11 is hydrogen, a phenyl or halophenyl radical; and R1 is hydrogen, a phenyl or halophenyl radical, a lower alkyl radical of not more than 6 carbon atoms, an alkoxy group of not more than 4 carbon atoms, an -amino group or a monosubstituted amino group; and the preparation of such compounds by reacting a pyrimidine derivative of the formula <FORM:0763043/IV(b)/2> with an alkali metal hydroxide, ammonia or a primary or secondary amine, or by reacting a pyrimidine derivative of the formula <FORM:0763043/IV(b)/3> with an a -amino-aldehyde, -ketone or -carboxylic acid ester or amide of the formula NH2CRR11COR1.  The amino-aldehyde or aminoketone may be used in the form of an acetal, oxime or semicarbazone, and the product subsequently hydrolysed.  In examples: (1) 4-chloro - 5 - p - chlorobenzeneazo - 6 - desylamino - 2 - dimethylaminopyrimidine, dimethylamine and ethanol are heated to give 5-p - chlorobenzenazo - 4 - desylamino - 2,6 - bisdimethylaminopyrimidine; (2) 4 - chloro - 5-p - chlorobenzeneazo - 2 - dimethylamino - 6-hydroxypyrimidine, glycine ethyl ester, ethanol and dimethylformamide are heated together to give ethyl 5 - p - chlorobenzeneazo - 2 - dimethylamino - 4 - hydroxy - 6 - pyrimidylaminoacetate; (3) ethyl - 4 - chloro - 5-p-chlorobenzeneazo - 2 - dimethylamino - 6-pyrimidylaminoacetate, methylamine and ethanol are heated together to give ethyl-5-p-chlorobenzeneazo - 2 - dimethylamino - 4-methylamino - 6 - pyrimidylaminoacet - N-methylamide; (4) 4-chloro-5-p-chlorobenzeneazo - 2 - dimethylamino - 6 - hydroxypyrimidine, aminoacetone semicarbazone, ethanol and dimethylformamide are heated together to give 5-chlorobenzeneazo - 2 - dimethylamino - 4-hydroxy - 6 - pyrimidylaminoacetone semi-carbazone which is then hydrolysed with hydrochloric acid to remove the semicarbazone group; (5) a  - amino - a  - phenyl - 4 - chloroacetophenone, 6 - chloro - 5 - p - chlorobenzeneazo - 2 - dimethylamino - 4 - hydroxypyrimidine, ethanol and dimethylformamide are heated together to give a  - phenyl - a  - (5 - p - chlorobenzeneazo - 2 - dimethylamino - 4 - hydroxy-6 - pyrimidylamino) - 4 - chloroacetophenone; (6) aminoacetal, 6 - chloro - 5 - p - chlorobenzeneazo - 2 - dimethylamino - 4 - methylaminopyrimidine and dioxan are heated together to give 5-p-chlorobenzeneazo-2-dimethylamino-4-methylamino - 6 - pyrimidylaminoacetal which is then hydrolysed to the corresponding aldehyde.  The preparation of other specific compounds within the general formula is described.  The Provisional Specification relates to pyrimidine derivatives of the above general formula wherein X and Y are hydrocarbon radicals which may be joined together to form a heterocyclic ring, B is a hydroxyl, alkoxy, thiol, alkylthio, amino or substituted amino group, R and R11 are hydrogen, hydrocarbon or substituted hydrocarbon radicals, or one of them may be a COR1 radical, R1 is hydrogen, a hydrocarbon radical or a hydrocarbonoxy radical or an amino or mono-substituted amino group and Ar is an aryl or substituted aryl group.  Specification 763,044 is referred to.