反应详情

温度

80 °C

(3,5-Bis-trifluoromethyl-benzyl)-(5-bromopyrimidin-2-yl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amine (3.0 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium methylene chloride complex (112 mg), potassium acetate (1.34 g) and bis(pinacolato)diboron (1.74 g) are dissolved in dimethylsulfoxide (20 ml) and the mixture is heated to 80° C. under nitrogen atmosphere and stirred for 1 hour. The reaction solution is cooled to room temperature, and thereto are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue is dissolved in tetrahydrofuran (70 ml) and thereto is added dropwise a 30% aqueous hydrogen peroxide solution (15 ml) under ice-cooling. One hour thereafter, thereto is added a saturated aqueous sodium thiosulfate solution under ice-cooling to consume the excess hydrogen peroxide, and thereto are added water and ethyl acetate, and the mixture is separated, and 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=19:1→3:1) to give 2-{(3,5-bis-trifluoromethyl-benzyl)-[2-(butyl-ethyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-ol (263 mg). MS (m/z): 595 [M+H]+

1. temperatureThe reaction solution is cooled to room temperature
2. customthe mixture is separated
3. washthe organic layer is washed with a saturated brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe resulting residue is dissolved in tetrahydrofuran (70 ml)
7. additionis added dropwise a 30% aqueous hydrogen peroxide solution (15 ml) under ice-
8. temperaturecooling
9. additionOne hour thereafter, thereto is added a saturated aqueous sodium thiosulfate solution under ice-
10. temperaturecooling
11. customto consume the excess hydrogen peroxide
12. additionare added water and ethyl acetate
13. customthe mixture is separated
14. washthe organic layer is washed with a saturated brine
15. dry with materialdried over magnesium sulfate
16. concentrationconcentrated under reduced pressure
17. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→3:1)