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Paper | Regular issue | Vol 34, No. 4, 1992, pp.713-722
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5888
5-Alkoxymethyl-1-hydroxyalkyluracils with Potential Anti-HIV Activity

Ahmed E.-S. Abdel-Megied, Mohammed S. Motawia, Erik B. Pedersen, and Carsten M. Nielsen

*Department of Chemistry, Odense University, DK-5230 Odense M, Denmark


Acid catalyzed etherification of 5-hydroxymethyluracil (3) afforded the corresponding 5-alkoxymethyluracils (4a-h). Treatment of the sodium salt of compounds (4a-g) with 4-bromobutyl acetate afforded 1,3-bis-(4-acetyloxybutyl)- (5a-g) and 1-4-acetyloxybutyluracil derivatives (6a-g). Alkylation of 4h with 5-chloropentyl benzoate gave 1,3-bis-(5-benzoyloxypentyl)- (8) and 1-(5-benzoyloxypentyl)-5-t-butyloxymethyluracil (9). Ammonolysis of 6a-g and 9 at room temperature gave the corresponding hydroxyalkyl derivatives (7a-g and 10).