5-Fluorouracil → Tegafur

In 10 ml of pyridine were dissolved 0.39 g of 5-fluorouracil and 0.42 g of 2,3-dihydrofuran. To the solution were added 72 mg of dimethylphenylsulfonium perchlorate and the mixture was reacted for 5 hours at 130° C. After the reaction, pyridine was distilled off under reduced pressure and 20 ml of water were added to the residue. The aqueous solution was treated with caustic soda to have a pH value of 10-11 and then washed with 20 ml of chloroform. The aqueous alkaline solution was treated while cold with diluted hydrochloric acid to adjust the pH value of the solution to 3.5 and then extracted three times with 20 ml of chloroform. The chloroform extract was dried and then the chloroform was distilled off. The residue was recrystallized from ethanol to obtain 0.35 g of 1-(2-tetrahydrofuryl)-5-fluorouracil. The yield was 58.3%.

1. customthe mixture was reacted for 5 hours at 130° C
2. distillationwas distilled off under reduced pressure and 20 ml of water
3. additionwere added to the residue
4. additionThe aqueous solution was treated with caustic soda
5. washwashed with 20 ml of chloroform
6. additionThe aqueous alkaline solution was treated while cold with diluted hydrochloric acid
7. extractionextracted three times with 20 ml of chloroform
8. extractionThe chloroform extract
9. customwas dried
10. distillationthe chloroform was distilled off
11. customThe residue was recrystallized from ethanol

ORD record

ord-3cbfbaf362014ecf9c3e60ffac67f835

Source dataset

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04256885