5-Fluorouracil → Tegafur

Participants

Reaction Steps

In 50 ml of pyridine were dissolved 2.5 g of 5-fluorouracil and 0.35 g of anhydrous aluminum chloride. To this solution were added 2.3 ml of 2,3-dihydrofuran and the mixture was reacted at 120° C. for 6 hours. A part of the reaction liquid was extracted and subjected to thin layer chromatography to observe the state of proceeding of the reaction whereby the composition of the product was 70% of the end product, 10% of by-products and less than 1% of unreacted 5-fluorouracil. The pyridine was distilled off from the reaction liquid and the residue was shaken with 50 ml of chloroform and a small amount of water and the mixture was separated. The chloroform layer was dried and the chloroform was distilled off. The precipitated crystals were collected by filtration, washed with ether and dried to obtain 2.9 g of 1-(2-tetrahydrofuryl)-5-fluorouracil in a yield of 75.4%, which had a melting point of 167°-168° C.

Provenance & Evidence