Sodium hydride → HCID 22347164, compound

Participants

Reaction Steps

A solution of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.200 g, 0.00079 mol) in N-methyl pyrrolidinone (10 mL) was reacted with 60% sodium hydride in oil (0.032 g, 0.00079 mol). After gas evolution ceased, the mixture was stirred at ambient temperature for 30 minutes, and 5-bromo-2-nitropyridine (0.161 g, 0.00079 mol) was added and heated at 40° C. for 18 hours. Additional 60% sodium hydride in oil (0.032 g, 0.00079 mol) was added and the mixture was stirred an additional 2 hours. The solvent was removed in vacuo and the residue was partitioned between dichloromethane (15 mL) and water (25 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×15 mL). The combined organics were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was purified by flash column chromatography on silica using heptane/ethyl acetate (1:2) as an eluent to give two products. The less polar compound, 1-(6-nitro-3-pyridyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine, was suspended in absolute ethanol (10 mL) and N,N-dimethylformamide (5 mL) and 10% palladium on carbon (0.007 g) was added. The mixture was stirred under a balloon atmosphere of hydrogen for 18 hours. The mixture was filtered through pad of Celite® 521, washing with absolute ethanol. The solvent was removed in vacuo to give 1-(6-amino-3-pyridyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.007 g, 0.00002 mol) as a white solid.

Provenance & Evidence