Synthesis of 1-(tetrahydro-2-furanyl)-5-fluorouracil (Ftorafur) via direct fluorination
US3948897A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Oct 9, 1973 |
| Grant date | Apr 6, 1976 |
| Priority date | — |
| Expiry date | Oct 9, 1993 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D405/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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).
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.