Potassium Carbonate → HCID 68108371, 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) (500 mg, 0.936 mmol), (3-amino-3-phenyl-propyl)-carbamic acid tert-butyl ester (from Example 2 supra) (328 mg, 1.31 mmol), Pd2(dba)3 (54 mg, 0.094 mmol), DavePhos (74 mg, 0.187 mmol), K2CO3 (181 mg, 1.31 mmol) and dioxane (20 mL). The mixture was stirred at 132° C. under an atmosphere of N2 for 7.5 hours. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 14 g, 100-200 mesh, eluting with dichloromethane:MeOH, 80:1) to give crude product which was further purified by prep-HPLC to afford (3-{6-[6-(2-morpholin-4-yl-ethylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-pyridin-2-ylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester. (Yield 147 mg, 16%).

Provenance & Evidence