Sodium Hydroxide → 2-[4-(4-Fluorobenzoyl)benzyl]thio-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

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Reaction Steps

In methanol (25 ml) was suspended 5-methyl-2-mercapto-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one (1.82 g) followed by addition of 1N-sodium hydroxide (10.5 ml) for dissolution. Then, under ice-cooling, a solution of 4-(4-fluorobenzoyl)benzyl bromide (3.51 g) in DME (10 ml) was added dropwise. The mixture was stirred at room temperature for 4 hours and the resulting crystalline precipitate was collected by filtration and rinsed with water. The crystals were further rinsed with 50% ethanol/water, methanol and ether serially, dried, and recrystallized from DME (1,2-dimethoxyethane) to provide the title compound (2.71 g). 1H-NMR (DMSO-d6) δ: 2.24(3H,s), 4.51(2H,s), 6.65(1H,s), 7.37(2H,t,J=8.8Hz), 7.64(2H,d,J=8.8Hz), 7.70(2H,d,J=8.8Hz), 7.81(2H,dd,J=5.6,8.8Hz), 11.43(1H,s), 11.97(1H,s).

Provenance & Evidence