Acetic Acid → HCID 86665099, compound

Participants

Reaction Steps

1-(2-Chlorofuro[3,2-d]pyrimidin-4-yl)piperidine-4-carbaldehyde (0.672 g, 2.53 mmol; Preparation #P.1), 2,2-difluoroethanamine (0.226 g, 2.78 mmol, Matrix), and AcOH (0.217 mL, 3.79 mmol) were combined in DCE (25.3 mL) at rt. After about 10 min of stirring, NaBH(OAc)3 (0.804 g, 3.79 mmol) was added in one portion and the mixture was stirred for about 24 h. The mixture was diluted with DCM (50 mL) and saturated aqueous NaHCO3 (50 mL). The layers were separated and the aqueous layer extracted with DCM (3×15 mL). The combined organics were then washed with saturated aqueous NaHCO3 (25 mL), brine (25 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography (80 g silica gel, 50-100% EtOAc/heptane) to provide N-((1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methyl)-2,2-difluoroethanamine (0.748 g, 89%): LC/MS (Table 2, Method c) Rt=1.52 min.; MS m/z: 331, 333 (M+H)+.

Provenance & Evidence