Nucleosides and Nucleotides. V. Identification and Substitution Reaction of 1-Methyl-2, 4-dialkoxypyrimidinium Salts : Model Studies on Hilbert-Johnson Pyrimidine Nucleoside Synthesis

Abstract

Methylation of 2, 4-dialkoxypyrimidines with methyl iodide gave the reactive 1-methyl-pyrimidinium salts, the intermediates to 1-methyl-4-alkoxy-2-pyrimidinones. The isolation of the 1-methylpyrimidinium salt verifies the postulated mechanism of the Hilbert-Johnson reaction for pyrimidine nucleoside synthesis. The results of the substitution reaction of various 2, 4-disubstituted 1-methylpyrimidinium salts are described and the device of the extension of the Hilbert-Johnson procedure for the general method of the synthesis of 2-substituted pyrimidine nucleosides is discussed.