Studies on Functionally-substituted Azines. 8. Synthesis and Transformations of 1-Arylsulfonylamido-4-methoxy-6-methylpyrimidines

The action of arylsulfonyl chlorides on 2-amino-4-methoxy-6-methylpyrimidine in pyridine gave 2-arylsulfonylamido-4-methoxy-6-methylpyrimidines, which were alkylated at the amide fragment, while the action of hydrazine hydrate led to nucleophilic replacement of the methoxy group. The resultant hydrazinopyrimidines were converted into azidopyrimidines and N-pyrimidinyldithiocarbazinates. Potassium salt of 2-p-toluenesulfonylamido-4-methoxy-6-methylpyrimidine dithiocarbazinate reacted with dimethyl sulfate to give the S-methyl derivative, while the reaction with chloroacetonitrile gave thiazolidinylaminopyrimidine. The chlorination using N-chlorosuccinimide yielded only 5-chloropyrimidines.