反应详情

A mixture of methyl 2-(2-((tert-butoxycarbonylamino)methyl)piperidin-1-yl)-4-cyano-6-(m-tolylamino)pyrimidine-5-carboxylate (310.1 mg, 0.645 mmol), palladium on carbon (72.4 mg, 0.680 mmol) in EtOH (8 mL), and 1N HCl (4 mL) was stirred at RT for 16 h. The mixture was filtered to remove the catalyst. The filtrate was treated with saturated aq NaHCO3 (20 mL) for 3 h. The mixture was concentrated under reduced pressure and the residue was extracted with EtOAc (2×40 mL). The organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL), and brine (20 mL), were dried over anhydrous Na2SO4, and then filtered through SiO2. The filtrate was concentrated under reduced pressure to give the title compound as a colorless solid (213.4 mg, 73%). 1H-NMR (DMSO-d6) δ ppm 1.28 (s, 9H), 1.35 (br s, 1H), 1.49-1.56 (m, 2H), 1.67-1.69 (m, 3H), 2.31 (s, 3H), 3.06 (br s, 1H), 3.24 (br s, 2H), 4.16 (s, 2H), 4.67 (br s, 1H), 5.08 (br s, 1H), 6.77 (br s, 1H), 6.87 (d, 1H, J=7.0 Hz), 7.23-7.25 (m, 1H), 7.53 (br s, 2h), 8.07 (s, 1H), 8.55 (s, 1H). [M+H] calc'd for C24H33N6O3, 453; found, 453.5.

1. filtrationThe mixture was filtered
2. customto remove the catalyst
3. additionThe filtrate was treated with saturated aq NaHCO3 (20 mL) for 3 h
4. concentrationThe mixture was concentrated under reduced pressure
5. extractionthe residue was extracted with EtOAc (2×40 mL)
6. washThe organic layers were washed with saturated aq NaHCO3 (20 mL), water (20 mL), and brine (20 mL)
7. dry with materialwere dried over anhydrous Na2SO4
8. filtrationfiltered through SiO2
9. concentrationThe filtrate was concentrated under reduced pressure