Cesium carbonate → 4-(4-methanesulfonyl-phenoxy)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

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Reaction Conditions

Reaction Steps

4-(Methylsulfonyl)-phenol (Oakwood Products, Inc., West Columbia, S.C., USA; 516 mg, 3 mmol) and cesium carbonate (1.63 g, 5 mmol) were added to a solution of 4-chloro-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (from Step 1; 610 mg, 2.56 mmol) in dimethylformamide (15 mL). The mixture was heated at 90° C. for 1 h, then cooled, poured into saturated aqueous sodium bicarbonate solution, and extracted three times with ethyl acetate. The combined organic extracts were washed with twice with water and once with brine, dried (magnesium sulfate), filtered, and evaporated to give 4-(4-methanesulfonyl-phenoxy)-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine (780 mg, 58%).

Provenance & Evidence