Water → [3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine

Participants

Reaction Steps

SEM-Cl (5.15 g, 30.9 mmol) was added dropwise to a solution of 3-(6-bromo-pyridin-2-yl)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine (from Example 30 supra) (8.0 g, 25.8 mmol) and TEA (10.4 g, 103 mmol) in DMF (170 mL). The reaction was stirred at room temperature for 40 minutes. Then 2-morpholinoethanamine (4.03 g, 30.9 mmol) was added dropwise to the above solution. The mixture was heated at 55° C. for 12 hours. After cooling to room temperature, the reaction mixture was poured into water (500 mL) and extracted with ethyl acetate. Ethyl acetate solution was evaporated and purified by chromatography (silica gel, dichloromethane:MeOH, 50:1) to afford [3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-(2-morpholin-4-yl-ethyl)-amine as yellow solid. (Yield 5.6 g, 41%).

Provenance & Evidence