反应详情

温度

60 °C

2-Chloro-5-bromopyrimidine (5.0 g, 26 mmol), 2-methyl-4-ethynyl-1,3-thiazole (3.2 g, 26 mmol), tetrakis(triphenylphosphine)palladium(0) (0.6 g, 0.5 mmol), copper(I) iodide (0.1 g, 0.5 mmol) and triethylamine (13 g, 130 mmol) were added to deoxygenated toluene (50 mL) at room temperature. The reaction was then warmed to 60° C. Stirring continued for 2.5 hrs and the reaction contents were then poured in to a separatory funnel and partitioned with EtOAc (100 mL) and water (100 mL). The organic layer was then washed with water twice (250 mL each). The organic layer were dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was chromatographed on SiO2, eluting with 1:1 EtOAc:hexanes to afford 2-chloro-5-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyrimidine as a tan solid. 1H-NMR (CDCl3, 300 MHz) δ 8.78 (s, 2H), 7.52 (s, 1H), 2.78 (s, 3H).

1. customto deoxygenated toluene (50 mL) at room temperature
2. customthe reaction contents
3. additionwere then poured in to a separatory funnel
4. custompartitioned with EtOAc (100 mL) and water (100 mL)
5. washThe organic layer was then washed with water twice (250 mL each)
6. dry with materialThe organic layer were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude residue was chromatographed on SiO2
10. washeluting with 1:1 EtOAc