Studies on Pyrimidine Derivatives and Related Compounds. XLIX. Several Reactions of 1-[(2-Methyl-4-amino-5-pyrimidinyl) methyl]-3-alkyl-4-(2-hydroxyethyl)-5-methyl-imidazolium Salts.

Abstract

1-[(2-Methyl-4-amino-5-pyrimidinyl) methyl]-3-alkyl-4-(2-hydroxyethyl)-5-methylimidazolium salts reacted with diethyl benzoylphosphonate after treatment with triethylamine to give O-benzoate. However, the treatment with dimethylsulfinyl carbanion in dimethylsulfoxide gave iminochrome type compounds (VI, XIX), imidazole (XXVI), and azomethine compounds (VII, XX, XXVIII). The difference of lability between imidazolium and thiazolium C-2 protons was shown by NMR measurements.