Acetic Acid → HCID 118131118, compound

Participants

Reaction Steps

3-(3-(1-(4-amino-3-(3-fluoro-5-hydroxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-1-oxo-1H-isochromen-4-yl)benzaldehyde (Intermediate F2, 598 mg, 1.147 mmol), AcOH (131 μl, 2.293 mmol) and 2M dimethylamine (1.15 ml) solution in THF were dissolved in DCM (23 ml) followed by a spoon of anhydrous Na2SO4, and the mixture stirred rt for 15 min prior to add NaB(OAc)3H (1215 mg, 5.73 mmol). The resulting mixture was stirred at rt until complete conversion, then quenched with 1M HClaqueous (5 ml), filtered to remove insoluble materials, and the filtrate purified via reverse phase chromatography using a Biotage C18 60 g SNAP with a gradient of water and acetonitrile to give (prior to drying a small amount of 1M HCl aqueous was added) the title compound (460 mg, 68.3% yield) as white solid.

Provenance & Evidence