STUDIES ON FUNCTIONALLY-SUBSTITUTED AZINES. 8. SYNTHESIS AND TRANSFORMATIONS OF 1-ARYLSULFONYLAMIDO-4-METHOXY-6-METHYLPYRIMIDINES
DOI:
https://doi.org/10.1007/432Keywords:
azidopyrimidines, 2-arylsulfonylamidopyrimidines, dithiocarbazinates, S-methyl derivatives, S-cyanomethyl derivativesAbstract
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.
Authors: V. V. Dovlatyan and M. G. Hovhannisyan.
English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (11), pp 1306-1313
