Phosphorus oxychloride → 4-chloro-1-(2-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidine

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Reaction Conditions

Reaction Steps

Phosphoryl trichloride (34.2 ml, 356.88 mmol) was added to 1-(2-(trifluoromethyl)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ol (Intermediate P2) (5.0 g, 17.84 mmol). The resulting solution was stirred at 100° C. for 4 hours. The mixture was evaporated and the residue added to ice (˜200 g) with vigorous stirring. The mixture was stirred for 30 mins and the solid was collected by filtration washed with water (3×50 mL) and dried by suction. The solid was dissolved in ethyl acetate (250 mL), dried (MgSO4) and evaporated to give the product (4.5 g, 85%). 1H NMR (400 MHz, DMSO) δ 7.75-7.80 (1H, m), 7.88-7.91 (1H, m), 7.95-7.98 (1H, m), 8.05-8.07 (1H, m), 8.79 (1H, s), 8.88 (1H, s); m/z (ESI+) (M+H)+=299; HPLC tR=2.39 min.

Provenance & Evidence