Synthesis of 1-(tetrahydro-2-furanyl)-5-fluorouracil (Ftorafur)

Details Synthesis of 1-(tetrahydro-2-furanyl)-5-fluorouracil (Ftorafur) Synthesis of 1-(tetrahydro-2-furanyl)-5-fluorouracil (Ftorafur)

1973-10-09

1976-04-06

Gallagher, Richard J.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D23952

Patent

active

039488977

ABSTRACT:
A facile process for the production of Ftorafur [1-(tetrahydro-2-furanyl)-5-fluorouracil] which comprises reacting 2,4-bis-trimethylsilyl uracil with 2-chlorotetrahydrofuran to produce 1-tetrahydro-2-furanyluracil at low temperatures in a dry non-aqueous solvent, e.g. a halogenated hydrocarbon solvent such as methylene chloride. Subsequently the desired final product is produced by direct fluorination of the uracil ring as the last step utilizing a fluorinating agent such as trifluoromethylhypofluorite. This step is conducted in the cold and again in the presence of a halogenated hydrocarbon solvent such as chloroform. Ftorafur has been utilized as a pyrimidine analog for the management of carcinoma in the breast and large intestine and with less side effects than 5-fluorouracil (5-FU).

REFERENCES:
patent: 3682917 (1972-08-01), Kruniants

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