Sodium Bicarbonate → tert-Butyl (4-(5-((S)-1-((2-amino-5-cyano-6-methylpyrimidin-4-yl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)cyclohex-3-en-1-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (S)-2-amino-4-((1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-6-methylpyrimidine-5-carbonitrile (0.07 g, 0.181 mmol), tert-butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)carbamate (0.076 g, 0.236 mmol), PdCl2(dppf)-CH2Cl2 adduct (0.015 g, 0.018 mmol) and sodium bicarbonate (0.030 g, 0.362 mmol) in dioxane (2 mL) and water (0.500 mL). The reaction mixture was heated to 100° C. for 40 minutes in a microwave reactor. Following reaction, the solvent was removed under a nitrogen stream and the residue was partitioned between ethyl acetate (20 mL) and water (20 mL). The organic phase was dried over anhydrous sodium sulfate and purified on a silica gel column (20-80% ethyl acetate/heptanes gradient) to give the title compound as a tan solid (79 mg, 87%). ESI-MS m/z [M+H]+ calc'd for C27H34N8O2, 503. found 503.

Provenance & Evidence