Tetrahydrofuran → HCID 178505888, compound

Participants

Reaction Steps

To a neat sample of 2,4-difluorophenol (Aldrich) (379 mg, 3 eq) in a Microwave Reactor Vessel, at 0° C. was added dropwise a 1.0 M potassium tert-butoxide solution in THF (2.9 mL, 3.05 eq). The mixture was stirred 5 minutes and then warmed to room temperature. Solid 3-(2-chlorophenyl)-6-methylsulfonyl-1H-pyrazolo[3,4-d]pyrimidine (300 mg, 0.971 mmol) was added and the reaction mixture was placed in a Microwave Reactor and heated at 120° C. for 15 minutes. The reaction mixture was diluted with ethyl acetate (50 mL), saturated aqueous ammonium chloride (10 mL) and water (40 mL). The mixture was partitioned and the organic layer was collected. The aqueous layer was extract with ethyl acetate (40 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated to provide the crude compound. Purification by Preparative Thin Layer Chromatography eluting with 1.8% methanol in dichloromethane, followed by crystallization from methylene chloride/hexanes gave the title compound as a white powder (553 mg, (M+H)+=359, M.P.=173.4-176.4° C.).

Provenance & Evidence