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

Nucleosides, nucleotides & nucleic acids (2000-09-22)
U Henriksen
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Trimethylsilyl trifluoromethanesulfonate, purum, ≥98.0% (T)
Sigma-Aldrich
N,O-Bis(trimethylsilyl)acetamide, synthesis grade, ≥95%
Supelco
N,O-Bis(trimethylsilyl)acetamide, for GC derivatization, LiChropur, ≥98.5% (GC)
Sigma-Aldrich
Trimethylsilyl trifluoromethanesulfonate, 99%
Sigma-Aldrich
N6-Benzoyladenine, ≥99%