5,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-one → 3-[2-(2,4-Difluorophenyl)-2-hydroxy-3-[1,2,4]triazol-1-yl-propyl]-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3h)-one

Participants

Reaction Steps

5,6,7,8-Tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one of Formula (4-A09) (1.0 g, 4.8 mmole), 1[[2-(2,4-difluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole of the Formula (5) (1.38 g, 5.8 mmole) and sodium methoxide (0.31 g, 5.8 mmole), were taken in two neck round bottom flask under inert atmosphere, dry t-butanol (30 ml) was added to the above reaction mixture and the mixture was stirred under reflux for 12 hours. t-Butanol was removed on rotavapor, water (20 ml) was added to the reaction mixture, the compound from the reaction mixture was extracted with ethyl acetate (3×20 ml), dried, concentrated and purified by column chromatography to obtain the pure 3-[2-(2,4-Difluorophenyl)-2-hydroxy-3-[1,2,4]triazol-1-yl-propyl]-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one (1-A09) (1.29 gm, 60%). 1HNMR (CDCl3, 200 MHz): 1.74-1.96 (m, 4H), 2.71-2.81 (m, 2H), 2.90-3.02 (m, 2H), 4.18 (d, J=14 Hz, 1H), 4.55 (d, J=14 Hz, 1H), 4.70 (d, J=14 Hz, 1H), 4.77 (d, J=14 Hz, 1H), 6.29 (bs, 1H), 6.72-6.92 (m, 2H), 7.51-7.62 (m, 1H), 7.85 (s, 2H), 8.13 (s, 1H).

Provenance & Evidence