On the occurrence of the anrorc mechanism in aminations of substituted halogenoaza‐aromatics with potassium amide in liquid ammonia On the mechanism of the reaction of 4‐halogeno‐2,6‐diphenylpyrimidines and of 5‐bromo‐4‐chloro‐2,6‐diphenylpyrimidine with potassium amide in liquid ammonia

Abstract

Abstract Evidence is presented that the amination of 4‐chloro‐2,6‐diphenylpyrimidine with potassium amide in liquid ammonia into the corresponding 4‐amino compound occurs to the extent of about 45% by the ANRORC mechanism. In the amination of the 4‐iodo‐ and 4‐fluoro derivatives of 2,6‐diphenylpyrimidine, however, the ANRORC mechanism is not operative at all. The amination of 5‐bromo‐4‐chloro‐2,6‐diphenylpyrimidine into 4‐amino‐5‐bromo‐2,6‐diphenylpyrimidine occurs to the extent of about 18% by the ANRORC mechanism. The synthesis of 5‐bromo‐4‐chloro‐2,6‐diphenyl‐[1(3)‐ 15 N]pyrimidine and of the 4‐fluoro, 4‐chloro and 4‐iodo derivatives of 2,6‐diphenyl‐[1(3)‐ 15 N]pyrimidine is described.