5-Fluorouracil → Tegafur

Participants

Reaction Conditions

Reaction Steps

In an autoclave, 520 g of 5-fluorouracil, 1400 g of 2,3-dihydrofuran and 1.56 l of pyridine were heated together at 185° C. for 3 hours. After cooling, the reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in 6 l of ethanol-water(1:1). The solution was heated at 70° C. for 2 hours, after which it was treated with activated charcoal. After filtration, the solution was concentrated under reduced pressure to about one-half of its original volume. After cooling, the resultant crystals were recovered by filtration and dried. By the above procedure was obtained 780 g of 1-(tetrahydro-2-furyl)-5-fluorouracil. If necessary, this product may be recrystallized from ethanol. Recrystallization yielded 600 g of colorless needles, melting point: 167.5° C.

Provenance & Evidence