反应详情

trans-Dichlorobis(triphenylphosphine)palladium (II) (1.179 g, 1.680 mmol), 5-chloro-2-fluorophenylboronic acid (6.15 g, 35.3 mmol), 2-chloro-5-methylpyrimidin-4-amine (2.411 g, 16.80 mmol), were combined with 2M Na2CO3 (8.40 ml, 16.80 mmol) in dioxane (79 mL) and then heated at reflux for 1 hour. The reaction mixture was then cooled to room temperature and concentrated on a rotovap to afford a tan solid. The solid was suspended in brine (50 mL) and extracted with EtOAc (20 mL). The organic layer was dried over Na2SO4, filtered, and concentrated on a rotovap to afford an amber colored oil which was loaded onto silica (12 g) and purified by silica chromatography using a step gradient eluted with (10-75% ethyl acetate/hexanes) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.03 (3H, d, J=0.76 Hz) 6.85 (2H, br. s.) 7.31 (1H, dd, J=10.61, 8.84 Hz) 7.46-7.55 (1H, m) 7.88 (1H, dd, J=6.57, 3.03 Hz) 8.06 (1H, d, J=0.76 Hz). ESI-MS: m/z 238.1 (M+H).

1. temperatureheated
2. temperatureat reflux for 1 hour
3. concentrationconcentrated on a rotovap
4. customto afford a tan solid
5. extractionextracted with EtOAc (20 mL)
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated on a rotovap
9. customto afford an amber colored oil which
10. custompurified by silica chromatography
11. washeluted with (10-75% ethyl acetate/hexanes)