Studies on Pyrimidine Derivatives. XXI. Nucleophilic Substitution of 4-Chloropyrimidines and Related Compounds with Carbanions

Abstract

The reaction of 4-chloro-2, 6-dimethylpyrimidine 1-oxide (II) with ethyl cyanoacetate and malononitrile under basic conditions gave the expected condensation products, while the reaction of II with methylene ketones failed. On the other hand, 2, 6-dimethyl-4-phenylsulfonylpyrimidine (X) smoothyl reacted not only with the above active methyl compounds but also with methylene ketones such as acetone, acetophenone and cyclohexanone.