Nucleic Acids Research, 1977, Vol. 4, No. 9 3259-3266
© 1977
Articles |
Fluorination of 6-methyluracil and its nucleosides
aSektion Chemie, Humboldt Universität Berlin, GDR 166 10 Praha, Czechoslovakia bInstitute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Science 166 10 Praha, Czechoslovakia.
Received July 25, 1977. 6-Methyluracil and its perbenzoylated 1-(ß-D-ribofuranosyl) and 1-(2-deoxy-ß-D-ribofuranosyl) derivatives afford, on treatment with elemental fluorine in acetic acid solutions, the corresponding derivatives of 5-fluoro-6-methylurecil and 5-fluoro-6-fluoromethyluracil. The free nucleosides have been obtained from the protected derivatives by methanolysis. The CH2F linkage in 5-fluoro-6-fluoromethyluracil derivatives is stable towards hydrolysis and nucleophilic agents.