反应详情

N-(6-(2-fluoro-4-nitrophenoxy)pyrimidin-4-yl)pyrrolidine-1-carboxamide (0.320 g, 0.921 mmol) was dissolved in a mixture of 3:1 ethanol/water (8 ml). Then iron (0.276 g, 4.95 mmol) and ammonium chloride (0.0281 g, 0.525 mmol) was added to the mixture with stirring. The mixture was placed in a pre-heated oil bath (80° C.) for 1 hour. The oil bath was removed to allow the mixture to cool to ambient temperature. The mixture was filtered through a filter diskette. The flask was rinsed with methanol (3×10 ml) and filtered through diskette. Combined organic solution was concentrated in-vacuo. Then water was added to the mixture with stirring. The precipitate was collected by filtration and washed with hexanes. The solid was dried in a reduced-pressure oven to give the desired product N-(6-(4-amino-2-fluorophenoxy)pyrimidin-4-yl)pyrrolidine-1-carboxamide (0.240 g, 0.756 mmol, 82% yield) as a yellow solid. MS (ESI pos. ion) m/z: 318 (MH+). Calc'd exact mass for C15H16FN5O2: 317. 1HNMR (300 MHz, CDCl3): 1.91-2.05 (s, 4H), 3.41-3.54 (t, 4H), 6.41-6.52 (m, 2H), 6.92-7.01 (t, 1H), 7.21 (s, 1H), 7.63 (s, 1H), 8.36 (s, 1H).

1. customThe mixture was placed in a pre-heated oil bath
2. customThe oil bath was removed
3. filtrationThe mixture was filtered through a filter diskette
4. washThe flask was rinsed with methanol (3×10 ml)
5. filtrationfiltered through diskette
6. concentrationCombined organic solution was concentrated in-vacuo
7. additionThen water was added to the mixture
8. stirringwith stirring
9. filtrationThe precipitate was collected by filtration
10. washwashed with hexanes
11. customThe solid was dried in a reduced-pressure oven