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A New Synthetic Route to Polyalkoxypyrimidines Based on the Reaction of Esters and Methyl Thiocyanate
Author(s) -
Herrera Antonio,
MartínezAlvarez Roberto,
Ramiro Pedro,
Almy John,
Molero Dolores,
Sánchez Angel
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600222
Subject(s) - chemistry , thiocyanate , organic chemistry , alkoxy group , ring (chemistry) , pyrimidine , medicinal chemistry , stereochemistry , alkyl
Abstract 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)