Benzylamine → HCID 68108619, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with [3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine (from Example 32 supra) (150 mg, 0.28 mmol), benzylamine (42 mg, 0.39 mmol), Pd2(dba)3 (16 mg, 10% mmol), DavePhos (22 mg, 20% mmol), t-BuONa (37 mg, 0.39 mmol) and dioxane (10 mL). The mixture was stirred at 130° C. under an atmosphere of N2 for 6 hours. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, dichloromethane: MeOH, 100:1) to give [3-(6-benzylamino-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine. (Yield 90 mg, 57%).

Provenance & Evidence