A New Synthetic Route to Polyalkoxypyrimidines Based on the Reaction of Esters and Methyl...
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2006 Pyrimidine derivatives R 0510 A New Synthetic Route to Polyalkoxypyrimidines Based on the Reaction of Esters and Methyl Thiocyanate. — Reaction of aliphatic esters (I) and (IX) with methyl thio- cyanate (II) provides access towards alkoxy(bis(methylthio))pyrimidines (III) and (X), resp., in moderate to good yields. Various side products are observed, and for acetates, e.g. (IXa), thiocarbamates (XI) are the only products obtained. The methylthio groups can be replaced, after oxidation to the methylsulfonyl groups, with ammonia or sodium methoxide to furnish the target (amino)polyalkoxypyrimidines, e.g. (VIII) or (XIV). — (HERRERA, A.; MARTINEZ-ALVAREZ*, R.; RAMIRO, P.; ALMY, J.; MOLERO, D.; SANCHEZ, A.; Eur. J. Org. Chem. 2006, 15, 3332-3337; Dep. Quim. Org., Fac. Cienc. Quim., Univ. Complutense, E-28040 Madrid, Spain; Eng.) — Mischke 46- 197
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Transcript of A New Synthetic Route to Polyalkoxypyrimidines Based on the Reaction of Esters and Methyl...
2006
Pyrimidine derivativesR 0510 A New Synthetic Route to Polyalkoxypyrimidines Based on the Reaction of Esters
and Methyl Thiocyanate. — Reaction of aliphatic esters (I) and (IX) with methyl thio-cyanate (II) provides access towards alkoxy(bis(methylthio))pyrimidines (III) and (X), resp., in moderate to good yields. Various side products are observed, and for acetates, e.g. (IXa), thiocarbamates (XI) are the only products obtained. The methylthio groups can be replaced, after oxidation to the methylsulfonyl groups, with ammonia or sodium methoxide to furnish the target (amino)polyalkoxypyrimidines, e.g. (VIII) or (XIV). — (HERRERA, A.; MARTINEZ-ALVAREZ*, R.; RAMIRO, P.; ALMY, J.; MOLERO, D.; SANCHEZ, A.; Eur. J. Org. Chem. 2006, 15, 3332-3337; Dep. Quim. Org., Fac. Cienc. Quim., Univ. Complutense, E-28040 Madrid, Spain; Eng.) — Mischke
46- 197
