2,4-Dichlorophenol → HCID 820043, compound

Participants

Reaction Steps

First the substance of the formula (I) was synthetized from 4-chloro 2,6-diaminopyrimidine British patent specification No. 1,167,735; CA. 68, 21947h by heating the latter compound with 2,4-dichlorophenol at 150° C. in the presence of 85% aqueous potassium hydroxide solution to give 2,6-diamino-4-(2,4-dichlorophenoxy)pyrimidine. This substance was oxidized in a low yield to 6 amino 4-(2,4 dichlorophenoxy)-1,2-dihydro-1-hydroxy-2-iminopyrimidine, which was then transformed at 150° C. with piperidine to the target compound of the formula (I). The overall yield of this synthesis amounts to about 2.5% with a 45% yield in the last step. This is mainly caused by the fact that the replacement of the 2,4-dichlorophenoxy group by piperidine requires severe reaction conditions and long heating periods which favour unrequired side reactions, too.

Provenance & Evidence