Benzyl Alcohol → 4-(Benzyloxy)-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

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Reaction Steps

To a solution of benzyl alcohol (0.40 g, 3.7 mmol) in N,N-dimethylformamide (10 mL), sodium hydride (0.16 g, 40 mmol, 60% oil) was added at room temperature, and the resulting mixture was stirred at the same temperature for 30 minutes. To the solution, a solution of 4-chloro-N,3-dimethyl-N-phenyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide (1.0 g, 2.8 mmol) in N,N-dimethylformamide (10 mL) solution was added at room temperature, and stirred at 100° C. for 11.5 hours. The mixture was concentrated under reduced pressure, and the residue was poured into water. Organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Purification of the resulting residue by silica gel chromatography (hexane:chloroform:ethyl acetate=2:1:1 to 1:1:1 to 1:2:2) gave the title compound (0.99 g, 80% yield).

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