Acetic Acid → HCID 86677570, compound

Participants

Reaction Steps

To a solution of 4-(2-oxo-ethyl)-tetrahydro-pyran-4-carboxylic acid methyl ester (0.12 g, 0.644 mmol) in 1-2 dichloroethane (DCE, 6 mL) was added 2-chloropyrimidin-5-amine (0.084 g, 0.644 mmol), acetic acid (3.1 eq) and allowed to stir at room temperature for an hour. NaBH(OAc)3 (3 eq) was then added in one portion and reaction mixture allowed to stir at room temperature for 16 hours. The reaction was diluted with DCM (10 mL), quenched with 2 M of NH4OH in water (1 mL). The layers were separated, and the aqueous layer was extracted with DCM (10 mL, 2×). The combined organic layers were washed with aqueous NaHCO3 (10 mL), brine (20 mL), dried over Na2SO4, and concentrated under vacuum. Purification over silica gel eluting with ethyl acetate in heptanes (0-75%) afforded 0.088 g (46%) of title compound.

Provenance & Evidence