反应详情

To a 250-mL, round-bottomed flask containing 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (2.5 g, 9.7 mmol) and 7-hydroxyquinoline (2.0 g, 14 mmol, Acros) in DMF (30 mL), was added NaH (5.4 g, 14 mmol, 60% in mineral oil, Aldrich) at room temperature The solution was then stirred at room temperature for 4 h. After the solvent was removed in vacuum, EtOAc (100 mL) and water (50 mL) were added to the residue. The solid precipitate was filtered and the filtrate was poured into a separatory funnel. The organic layer was separated, combined with the previously isolated solid, concentrated in vacuum, and purified by silica gel chromatography (2:1 hexanes/EtOAc). The purified product was dissolved in acetone (30 mL) and MeOH (10 mL), and to the solution was added water (30 mL) in small portions. The precipitated solid was filtered, washed with water (5 mL), and dried under vacuum at 50° C. for 48 h to furnish the title compound as a white solid. Mp: 178–180° C. MS (ESI, pos. ion) m/z: 368 (M+1). Anal. Calcd for C20H12F3N3O: C, 65.40; H, 3.29; N, 11.44. Found: C, 65.42; H, 3.23; N, 11.43.

1. customAfter the solvent was removed in vacuum, EtOAc (100 mL) and water (50 mL)
2. additionwere added to the residue
3. filtrationThe solid precipitate was filtered
4. additionthe filtrate was poured into a separatory funnel
5. customThe organic layer was separated
6. concentrationconcentrated in vacuum
7. custompurified by silica gel chromatography (2:1 hexanes/EtOAc)
8. dissolutionThe purified product was dissolved in acetone (30 mL)
9. additionMeOH (10 mL), and to the solution was added water (30 mL) in small portions
10. filtrationThe precipitated solid was filtered
11. washwashed with water (5 mL)
12. customdried under vacuum at 50° C. for 48 h