Formaldehyde → HCID 73297209, compound

Participants

Reaction Steps

Formaldehyde (31.2 μL, 0.419 mmol, 37 wt % in H2O) was added to a suspension of 2-(2-(2-(5-chloro-2-((6-(piperidin-4-yl)pyridin-3-yl)amino)pyrimidin-4-yl)ethyl)phenyl)propanamide 37 (39.0 mg, 0.084 mmol) in MeOH (2.0 mL) under an atmosphere of nitrogen. Sodium triacetoxyborohydride (178 mg, 0.839 mmol) was added in one portion and the reaction mixture was stirred at room temperature for 2.5 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (10 mL) and sat. aq. NaHCO3 (10 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with water (20 mL) and brine (15 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting solid was suspended in DCM (20 mL) and cyclohexane (30 mL). The solid was filtered to give the title compound 38 (34 mg, 84%). LCMS-C: rt 4.19 min; m/z 479.2 [M+H]+.

Provenance & Evidence