反应详情

温度

80 °C

To a solution of 2-chloro-5-(trifluoromethyl)pyrimidine (0.300 g, 1.64 mmol) in dimethoxyethane (9 mL) was added a 2 M aqueous solution of sodium carbonate (3.7 mL, 7.4 mmol) and (5-(tert-butyl)-2-(methoxymethoxy)phenyl)boronic acid (0.500 g, 2.14 mmol). The solution was degassed with nitrogen for five minutes and tetrakis(triphenylphosphine)palladium(0) (95 mg, 0.082 mmol) was added and the reaction mixture heated to 80° C. in a sealed vial for 16 hours. The cooled reaction mixture was partitioned between ethyl acetate (25 mL) and 1 M aqueous sodium hydroxide solution (25 mL), the organic phase separated, dried (Na2SO4), filtered and concentrated under reduced pressure to give a yellow syrup. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes to give 2-(5-(tert-butyl)-2-(methoxymethoxy)phenyl)-5-(trifluoromethyl)pyrimidine (0.25 g, 44% yield) as a colorless oil.

1. customThe solution was degassed with nitrogen for five minutes
2. customThe cooled reaction mixture
3. customwas partitioned between ethyl acetate (25 mL) and 1 M aqueous sodium hydroxide solution (25 mL)
4. customthe organic phase separated
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto give a yellow syrup
9. customThe crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 100% ethyl acetate in hexanes