Syntheses of some pyrimidine N-oxides

Abstract
Various monosubstituted pyrimidines and methylpyrimidines were N-oxidized with a number of different peracids. In general, they are more susceptible to side reactions accompanying N-oxidation (i.e., decomposition, annular carbon oxidation, ring opening) than other -π-deficient diazine and triazine analogs. Unsymmetrical pyrimidines, which can potentially yield two isomeric products, were N-oxidized preferentially at the site para to strong electron-donating substituents. Weaker ring-activating groups, such as methyl, are mainly ortho directing and only aid in the N-oxidation of pyrimidine nuclei having ortho/para-directing substituents.

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