Thionyl Chloride → 5-(Azidomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

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Reaction Conditions

Reaction Steps

Thionyl chloride (SOCl2, 50.37 ml, 82.11 g, 69 mmol) was added dropwise over 15 minutes to a suspension of [1,6-d]ethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methanol (13.98 g, 46 mmol, e.g. which can optionally be as described in Intermediate 5) in toluene (140 ml) at room temperature. The mixture was then heated at reflux at about 85° C. for 4 hours, was allowed to cool, and then was evaporated to dryness and azeotroped with three further portions of toluene. The residue obtained was dissolved in dry dimethylsulfoxide (100 ml) and treated with sodium azide (4.49 g, 69 mmol), and the mixture was stirred at room temperature for 18 hours. The mixture was poured into saturated aqueous sodium bicarbonate solution and was extracted with 3 portions of ethyl acetate. The combined organic extracts were washed with saturated brine and water, and were then dried (Na2SO4), the drying agent was filtered off, and the filtrate was evaporated to dryness. The residue obtained was purified by flash chromatography, eluting with 1:1 cyclohexane:ethyl acetate. Fractions containing the product without substantial amounts of impurities were evaporated to give the title compound (5.6 g+4.75 g=10.35 g).

Provenance & Evidence