Tetrafluoroboric acid → HCID 178481919, compound

Participants

Reaction Steps

1-Methyl-1H-pyrazolo[3,4-d]pyrimidin-4-ol (5.50 g, 36.6 mmol) was combined with N-iodosuccinimide (97%, 12.7 g, 54.8 mmol) and tetrafluoroboric acid (50% solution in water, 23.0 mL, 183 mmol) in acetonitrile (50 mL) and the reaction mixture was heated to reflux for 5 hours. After cooling to room temperature, the reaction mixture was poured portion-wise into water (50 mL) containing sodium bicarbonate (18.6 g, 220 mmol). When gas evolution had ceased, the mixture was filtered, and the dark solid was washed successively with saturated aqueous sodium thiosulfate solution (25 mL) and water (2×25 mL). The resulting solid was dried under vacuum overnight at 50° C. to afford the product as a cream-colored solid. Yield: 9.35 g, 33.9 mmol, 93%. LCMS m/z 277.0 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 3.87 (s, 3H), 8.07 (s, 1H), 12.08 (v br s, 1H).

Provenance & Evidence