Potassium Carbonate → HCID 68108314, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with {4-[3-(6-bromo-pyridin-2-yl)-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (from Example 35 supra) (860 mg, 1.18 mmol), (2-amino-2-phenyl-ethyl)-carbamic acid tert-butyl ester (from Example 1 supra) (390 mg, 1.65 mmol), Pd2(dba)3 (68 mg, 0.12 mmol), DavePhos (93 mg, 0.24 mmol), K2CO3 (228 mg, 1.65 mmol) and dioxane (30 mL), this mixture was stirred at 132° C. under an atmosphere of N2 for 7 hours. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 26 g, 100-200 mesh, eluting with petroleum ether:ethyl acetate, 1:1) to give crude product which was further purified by prep-HPLC to afford (4-{3-[6-(2-tert-Butoxycarbonylamino-1-phenyl-ethylamino)-pyridin-2-yl]-1-trityl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino}-cyclohexyl)-carbamic acid tert-butyl ester. (Yield 103 mg, 9.86%).

Provenance & Evidence