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Synfacts 2006(8): 0775-0775
DOI: 10.1055/s-2006-941975
DOI: 10.1055/s-2006-941975
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Regioselective O- and N-Alkylation of Pyrimidine Nucleosides via the Mitsunobu Reaction
O. R. Ludek, C. Meier*
Universität Hamburg, Germany
Further Information
Publication History
Publication Date:
21 July 2006 (online)
Significance
The influence of the N3-substituent on the N1- versus O2- ambident alkylation regioselectivity of thymines 1 via the Mitsunobu reaction is reported. When N3-3,5-dinitrobenzoyl thymine was used as a nucleophile, alkylation proceeded with high N1-regioselectivity but in moderate chemical yield; alternatively, the N3-benzyloxymethyl group provides the product with good N1-regioselectivity in high yield. For O2-alkylation, the N3-2,6-dimethylbenzoyl group affords the O2-isomer exclusively in good yield.