A New Synthetic Route to Polyalkoxypyrimidines Based on the Reaction of Esters and Methyl Thiocyanate.

The reaction of aliphatic esters with methyl thiocyanate and triflic anhydride affords substituted 4-alkoxy-2,6-bis(methylthio)pyrimidines with minor amounts of substituted S-methyl N-alkanoylthiocarbamates. The structure of the starting ester appears to determine the ratio of final products. Methylthio groups on the pyrimidine ring can be easily converted into methylsulfonyl groups by oxidation. Controlled substitution of one or both methylsulfonyl groups leads to the formation of aminodialkoxy- and trialkoxypyrimidines. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)