Tetrahedron p. 3093 - 3100 (1990)
Update date:2022-07-29
Topics:
Stavber, Stojan
Zupan, Marko
1,3-Dimethyl and 1,3-dimethyl-5-halo substituted uracil derivatives reacted with CsSO4F under mild reaction conditions. Reactions carried out in an acetonitrile/water mixture or in a wide range of alcohols (methanol, ethanol, isopropanol and tert.butanol) resulted in the regioselective formation of the 5-fluoro-6-hydroxy or 5-fluoro-6-alkoxy-1,3-dimethyl-5,6-dihydrouracil derivatives, respectively, while the stereochemistry of the reaction was strongly syn predominant. Uracil was converted to 5-fluorouracil, and uridine to 5-fluorouridine, while the reaction of barbituric acid with CsSO4F in acetonitrile as solvent produced 5,5-difluorobarbituric acid.
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