反应详情

温度

110 °C

To a stirred solution of Bicyclo[1.1.1]pent-1-yl-(5-bromo-2-chloro-pyrimidin-4-yl)-amine (Preparation 280, 2 g, 7.29 mmol) in dry toluene (70 mL) was added (Z)-1-ethoxy-2-(tributylstannyl)ethene (2.7 mL, 8.03 mmol). The reaction mixture was purged with N2 for min and then Pd(PPh3)4 (421 mg, 0.36 mmol) was added, followed by degassing for another 20 min and heating to 110° C. under N2 overnight. The reaction was cooled to room temperature, quenched with a 2M solution of KF and filtered through a pad of Celite. The filtrate was partitioned between water (50 mL) and EtOAc (200 mL). The organic phase was washed with brine (2×25 mL), dried (Na2SO4) and evaporated in vacuo. The crude residue was purified by column chromatography on silica gel (EtOAc: Hexane 18: 82) to afford the title compound as a pale green solid in 77% yield, 1.5 g.

1. customThe reaction mixture was purged with N2 for min
2. customby degassing for another 20 min
3. temperatureThe reaction was cooled to room temperature
4. customquenched with a 2M solution of KF
5. filtrationfiltered through a pad of Celite
6. customThe filtrate was partitioned between water (50 mL) and EtOAc (200 mL)
7. washThe organic phase was washed with brine (2×25 mL)
8. dry with materialdried (Na2SO4)
9. customevaporated in vacuo
10. customThe crude residue was purified by column chromatography on silica gel (EtOAc: Hexane 18: 82)