Phosphorus oxychloride → 4-chloro-1-(5-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (5442 μl, 58.39 mmol) was added to 1-(5-fluoro-2-methylphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (Intermediate AK2) (713 mg, 2.92 mmol), at ambient temperature. The resulting mixture was heated to 100° C. and stirred for 4 hours. The mixture was allowed to cool to ambient temperature. The reaction mixture was evaporated to near dryness. Dissolved into toluene, evaporated, dissolved, in toluene and evaporated to dryness again. The solid was dried under vacuum to give crude product. This was partitioned between EtOAc (70 mL), and water (25 mL). The organic phase was dried (MgSO4), evaporated, then dried under vacuum to afford the product (732 mg, 95%). 1H NMR (400 MHz, DMSO) δ 2.13 (3H, s), 7.52-7.42 (2H, m), 7.64-7.58 (1H, m), 8.83 (1H, s), 8.96 (1H, s); m/z (ES+) (M+H)+=263; HPLC tR=2.39 min.

Provenance & Evidence