Dimethylformamide → 4-Chloro-2-(2-fluorophenyl)thieno[2,3-d]pyrimidine

反応式

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][S:14][C:12]=2[N:13]=1.S(Cl)([Cl:20])=O.CN(C)C=O>C(Cl)(Cl)Cl>[Cl:20][C:10]1[C:11]2[CH:16]=[CH:15][S:14][C:12]=2[N:13]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:9]=1

参加物

実験手順

2-(2-Fluoro-phenyl)-3H-thieno[2,3-d]pyrimidin-4-one (900 mg, 3.65 mmole) was dissolved in chloroform and thionyl chloride (0.532 ml, 7.30 mmole) was added to the mixture followed by 1 ml dimethylformamide. The reaction mixture was heated to reflux for 2.5 hours, the cooled mixture was washed with 10% sodium carbonate, the chloroform solution was dried over sodium sulfate (anh) and the solvent was removed. The crude product was chromatographed on silica gel, eluting with chloroform. Upon removal of solvent 438 mg of product was obtained (yield: 45%).