[F:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[Sb](Cl)(Cl)Cl.[O:14]1[CH:18]=[CH:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[O:14]1[CH2:15][CH2:16][CH2:17][CH:18]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[N:4]([CH:15]2[CH2:16][CH2:17][CH2:18][O:14]2)[C:5]1=[O:8].[O:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[N:6]1[CH:7]=[C:2]([F:1])[C:3](=[O:9])[NH:4][C:5]1=[O:8]In a sealed tube, 780 mg (6 m mole) of 5-fluorouracil, 5 ml of pyridine, 100 mg (0.44 m mole) of antimony trichloride and 1.26 g (18 m mole) of 2,3-dihydrofuran were heated at 100° C for 3 hours. The reaction mixture was further admixed with 800 mg (11.5 m mole) of 2,3-dihydrofuran and the mixture was heated for 17 hours. After the reaction, pyridine was distilled off under a reduced pressure and the residue was dissolved in chloroform and the insoluble matters were separated by a filtration. Chloroform was distilled off from the filtrate and the residue was purified by a column chromatography using a silica gel column (mixture of chloroform and acetone = 8 : 1 (V/V) as a developing medium) to obtain 1.10 g of N1,N3 -bis(2-tetrahydrofuryl)-5-fluorouracil (yield: 68.0%) and 325 mg of N1 -(2-tetrahydrofuryl)-5-fluorouracil (yield: 27%).
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