Acetonitrile → (S)-4-Amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylsulfonyl)pyrimidine-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a round-bottomed flask was added (S)-4-amino-6-((1-(1-methyl-6-(1-methyl-1H-pyrazol-5-yl)-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)amino)-2-(methylthio)pyrimidine-5-carbonitrile (200 mg, 0.477 mmol) in acetonitrile (5418 μL) and water (5418 μL). The mixture was cooled to 0° C. Oxone® (733 mg, 1.192 mmol) was added to give an orange solution. The reaction mixture was stirred at 0° C. for 30 min and then allowed to warm to room temperature. After 2 h, LCMS showed the reaction to be complete. The reaction mixture was subsequently diluted with EtOAc and washed with brine (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated to give the title compound as a yellow solid. ESI-MS m/z [M+H]+ calc'd for C20H21N9O2S, 452.15; found 452.4.

Provenance & Evidence