Nucleosides, Nucleotides & Nucleic Acids 2000-07-01

Facile synthesis of N-(1-alkenyl) derivatives of 2,4-pyrimidinediones.

U Henriksen

Index: Nucleosides Nucleotides Nucleic Acids 19 , 1093-1100, (2000)

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Abstract

N-(1-alkenyl) derivatives of 2,4-pyrimidinediones (6-9) were prepared in a one pot synthesis from aldehydes and the nucleobases using trimethylsilyl trifluoromethanesulfonate (TfOTMS) as coupling reagent. Presilylation of the above nucleobases, and N6-benzoyladenine, with excess N,O-bis(trimethylsilyl)acetamide (BSA) followed by addition of one mol eq. TfOTMS yielded the N-(1-trimethylsilyloxyalkyl) derivatives 1-5.