反应详情

N-(4-Bromo-2-methoxy-5-nitrophenyl)-4-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (Intermediate 138, 944 mg, 2.12 mmol), iron (710 mg, 12.7 mmol) and NH4Cl (85 mg, 1.59 mmol) were heated in ethanol (40 mL) and water (13 mL) at reflux for 1.5 h. The mixture was then cooled and filtered. The residue was triturated in 10% CH3OH in CH2Cl2 (30 mL) for 15 minutes and then filtered. The residues were triturated again with 10% CH3OH in CH2Cl2 (30 mL) and filtered. The combined filtrates were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification by FCC, eluting with 0-5% CH3OH in CH2Cl2 gave the title compound (814 mg, 92%) as a brown solid after trituration with diethyl ether; 1H NMR: 1.80-1.87 (2H, m), 1.96-2.03 (2H, m), 3.13 (2H, t), 3.77 (3H, s), 4.12 (2H, t), 4.82 (2H, s), 7.02 (1H, s), 7.05 (1H, d), 7.75 (1H, s), 7.77 (1H, s), 8.10 (1H, s), 8.34 (1H, d); m/z: ES+ MH+ 415/417.

1. temperatureThe mixture was then cooled
2. filtrationfiltered
3. customThe residue was triturated in 10% CH3OH in CH2Cl2 (30 mL) for 15 minutes
4. filtrationfiltered
5. customThe residues were triturated again with 10% CH3OH in CH2Cl2 (30 mL)
6. filtrationfiltered
7. washThe combined filtrates were washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. customPurification by FCC
11. washeluting with 0-5% CH3OH in CH2Cl2