反应详情

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.

1. stirringto stir at room temperature for 16 hours
2. customquenched with 2 M of NH4OH in water (1 mL)
3. customThe layers were separated
4. extractionthe aqueous layer was extracted with DCM (10 mL, 2×)
5. washThe combined organic layers were washed with aqueous NaHCO3 (10 mL), brine (20 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under vacuum
8. customPurification over silica gel eluting with ethyl acetate in heptanes (0-75%)