CH281435A - Process for the preparation of a new pyrimidine derivative. - Google Patents

Description

  

  Process for the preparation of a new pyrimidine derivative. The subject of the patent is a process for the production of a new pyrimidine derivative, namely 2- (3'-oxy-4'-earboxy-plienylaniino) -4,6-dimethyl-pyriinidine, which is used as an intermediate for the production of medicaments should be used again.

   The procedure is characterized by the fact that a compound of the formula
EMI0001.0013
         in which R denotes a group which can be converted into the carboxyl group by hydrolysis, condensed with acetylacetone, and the group R in the condensation product is converted into the carboxyl group by hydrolysis. This condensation can be carried out in the presence or absence of solvents.

    Acetyl acetone can also be used in excess as a solvent or diluent.



  The conversion of the group R. into the carboxyl group can be acidic or alkaline. A preferred embodiment of the process consists in reacting a 3-oxy-4- <# @ irlialkoxy-plienyl-guanidine with acetylene in excess.

   The 2- (3'-oxy-4'-earbalkoxy-phenylamino) -4,6-dimethyl-pyrimidine can then be converted into the 2- (3'-oxy-4'-carboxy by heating with a dilute alkali lye -phenylamino) -4,6-dimethyl-pyrimidine are converted.



  The 2- (3'-oxy-4'-carboxy-phenylamino) -4,6-dimethylpyrimidine thus obtained melts at 294 with decomposition, is easily soluble in dilute alkalis and sparingly soluble in water, methanol and ethanol.



  <I> Example: </I> 20 g of 3-oxy-4-carbomethoxy-phenylguanidine and 1.50 g of acetylacetone are boiled for 5 to 6 hours on the reflux condenser. The clear solution is brought to dryness in vacuo and the residue is recrystallized from 800 cm3 of alcohol.

   This gives 18 g of 2- (3'-oxy-4'-carbomethoxy-phenylamino) -4,6-dimethyl-pyrimidine which melts at 170 to 171 with partial sublimation. The compound dissolves easily in hot acetone, chloroform, ethyl acetate, benzene and chlorobenzene.



  8.8 g of the pyrimidine thus obtained are with. 65 ems n sodium hydroxide solution heated on the steam bath for about an hour. 3lan mixed with charcoal, filtered and acidified the blow filtrate with hydrochloric acid to pH 4.5. The precipitated crystals are filtered off with suction and reprecipitated from dilute ammonia with hydrochloric acid.

   7.5 g of 2- (3'-oxy-4'-carboxy-phenyl-amino) -4,6-dimethyl-pyrimidine which melts at 294 with decomposition are obtained. The new compound is easily soluble in dilute alkalis, but little in water, methanol and ethanol.

 

Claims (1)

PATENT CLAIM: Process for the preparation of a new pyrimidine derivative, characterized in that a compound of the formula EMI0002.0003 where R. denotes a group which can be converted into the carboxyl group by hydrolysis, condenses with acetylacetone, and the group R in the condensation product is converted into the carboxyl group by hydrolysis. The 2- (3'-oxy-4'-carboxy-phenyl-amino) -4,6-dimethyl-pyrimidine thus formed melts at 294 with decomposition. Easily soluble in dilute alkalis and sparingly soluble in methanol and ethanol. The new pyrimidine compound is to be used as an intermediate product in the manufacture of drugs. SUBCLAIMS: 1. Process according to claim, characterized in that a 3-oxy-4-carbalkoxy-phenylguanidine is condensed with acetylacetone and the 2- (3'-oxy-4'-carbalkoxy-phenylamino) -4, 6 - dimethyl - pyrimidine converted hydrolytically into the 2- (3'-oxy-4'-carboxy-phenylamino) -2,6-dimethyl-pyrimidine. 2. Process according to claim and sub-claim <B> 1., </B> characterized in that 3-oxy-4-carbomethoxy-phenylguanidine is heated with excess acetylacetone and the 2- (3'-oxy-4'- carbomethoxyphenylamino) -4,6-dimethirl-pyrimidine converted into 2- (3'-oxy-4'-carboxy-phenylamino) -4,6-dimethyl-pyrimidine by heating with dilute sodium hydroxide solution.