Water → (3-amino-2-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

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Reaction Steps

To (2-fluoro-3-nitro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-5-y)-methanone (38, 0.581 g, 2.03 mmol) in 20 mL of ethanol and 20 mL of tetrahydrofuran, stannous chloride dihydrate (1.58 g, 7.00 mmol) was added and the reaction placed in an oil bath at 60° C. After 2 hours, the reaction was poured into a beaker with 75 mL each of water and saturated sodium bicarbonate and 100 mL of ethyl acetate. The resulting milky suspension was treated with celite and the suspension was vacuum filtered through a thin pad of celite. The resulting clear layers of the filtrate were separated and the ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with a gradient of 1-6% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (39, 312 mg). MS (ESI) [M+H+]+=257.2.

Provenance & Evidence