Potassium Carbonate → HCID 68108456, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with {4-[3-(6-bromo-pyridin-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (from Example 33 supra) (618 mg, 1.0 mmol), (3-amino-3-phenyl-propyl)-carbamic acid tert-butyl ester (from Example 2 supra) (300 mg, 1.2 mmol), DavePhos (78 mg, 0.20 mmol), K2CO3 (166 mg, 1.2 mmol), Pd2(dba)3 (44 mg, 0.05 mmol) and 1,4-dioxane (20 mL). The mixture was stirred at 130° C. for 8 hours under an atmosphere of N2. The mixture was cooled and filtered. The filtrate was evaporated under reduced pressure and the residue was purified first by column chromatography (ethyl acetate:petroleum ether, 1:3), then by prep-HPLC to give {4-[3-[6-(3-tert-butoxycarbonylamino-1-phenyl-propylamino)-pyridin-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester. (Yield 71 mg, 9.0%).

Provenance & Evidence