反应详情

温度

50 °C

To a solution of tert-butyl 3-(6-(dibenzylamino)-5-nitropyrimidin-4-ylamino)phenylcarbamate (2) (9.2 g, 17.5 mmol) in 100 mL THF were added Fe powder (9.8 g, 175 mmol), NH4Cl (18.7 g, 350 mmol), 100 mL MeOH and 20 mL H2O. The reaction mixture was heated at 50° C. for 7 hrs under N2. After cooling to rt, the reaction mixture was filtered through a pad of Celite. The filtrate was concentrated to 100 mL, and extracted with EtOAc (80 mL×3). The combined organic layer was washed with water (100 mL×2) and brine (100 mL×1), dried over Na2SO4, then concentrated to dryness in vacuo. The residual was purified by column chromatography (silica gel, 0 to 30% ethyl acetate in petroleum ether) to give tert-butyl 3-(5-amino-6-(dibenzylamino)pyrimidin-4-ylamino)phenylcarbamate (3) (4.0 g, 46.1%) as a brown solid. LC-MS (ESI): m/z (M+1) 497.

1. temperatureAfter cooling to rt
2. filtrationthe reaction mixture was filtered through a pad of Celite
3. concentrationThe filtrate was concentrated to 100 mL
4. extractionextracted with EtOAc (80 mL×3)
5. washThe combined organic layer was washed with water (100 mL×2) and brine (100 mL×1)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to dryness in vacuo
8. customThe residual was purified by column chromatography (silica gel, 0 to 30% ethyl acetate in petroleum ether)