Heterocyclic studies. Part XII. Trichloro-6-cyanopyrimidine
Abstract
Treatment of 4-carbamoyl-2,6-dihydroxy-5-nitropyrimidine (I; X = CONH2) with phosphoryl chloride and diethylaniline unexpectedly yielded 2,4,5-trichloro-6-cyanopyrimidine (III; X = CN) together with 4-carbamoyl-2,6-dichloro-5-nitropyrimidine (II; X = Cl, Y = CONH2) and a little 2-chloro-4-cyano-6-N-ethylanilino-5-nitropyrimidine (II; X = NEtPh, Y = CN). Some of the trichloro-cyano-pyrimidine was also obtained by treatment of the pyrimidine (I; X = CONH2) with phosphoryl chloride in the presence of dimethylaniline, pyridine, triethylamine, or phosphorus pentachloride.
Nucleophilic substitution reaction of trichloro-6-cyanopyrimidine, in which the cyano-group was often displaced first, or modified, are described.