反应详情

温度

80 °C

(2-Benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amine (12.9 g) is dissolved in dimethylsulfoxide (150 ml), and thereto are added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (3.17 g), potassium acetate (5.71 g) and bis(pinacolato)diboron (9.85 g), and the mixture is heated to 80° C. under nitrogen atmosphere for 1 hour and 30 minutes. The reaction solution is cooled to room temperature, and thereto are added a saturated brine and ethyl acetate, and the mixture is separated, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is dissolved in tetrahydrofuran (150 ml), and thereto is added dropwise a 30% aqueous hydrogen peroxide solution (40 ml) under ice-cooling. Two hours thereafter, thereto is added a saturated aqueous sodium thiosulfate solution to consume the excess hydrogen peroxide, and thereto is added ethyl acetate, and the mixture is separated. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3) to give 2-[(2-benzyloxy-5-trifluoromethyl-benzyl)-(3,5-bis-trifluoromethyl-benzyl)-amino]-pyrimidin-5-ol (7.68 g). MS (m/z): 602 [M+H]+

1. temperatureThe reaction solution is cooled to room temperature
2. customthe mixture is separated
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. dissolutionThe resulting residue is dissolved in tetrahydrofuran (150 ml)
6. additionis added dropwise a 30% aqueous hydrogen peroxide solution (40 ml) under ice-
7. temperaturecooling
8. additionTwo hours thereafter, thereto is added a saturated aqueous sodium thiosulfate solution
9. customto consume the excess hydrogen peroxide
10. additionis added ethyl acetate
11. customthe mixture is separated
12. washThe organic layer is washed with a saturated brine
13. dry with materialdried over magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 7:3)