反应详情

温度

85 °C

5-((2-chloropyridin-4-yl)oxy)pyrimidin-2-amine (676 mg, 3.04 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (758 mg, 3.64 mmol), potassium carbonate (1.259 g, 9.11 mmol) and tetrakis(triphenylphosphine)palladium(0) (175 mg, 0.152 mmol) were combined in dioxane (12 mL) and water (3 mL). The mixture was degassed with argon, sealed and warmed to 85° C. overnight. The mixture was diluted with EtOAc (75 mL) and water (40 mL) and was filtered to collect an off-white solid. The organic phase was separated, washed with brine (40 mL) and evaporated at reduced pressure to give additional off-white solid. The two crops of solids were combined and triturated with EtOAc (15 mL) with sonication. The solid was collected by filtration, washed with EtOAc (2×5 mL) and dried under vacuum to provide 5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyrimidin-2-amine (455 mg, 55%). 1H NMR (DMSO-d6): δ 8.34 (d, J=5.7 Hz, 1 H), 8.26 (s, 1 H), 8.22 (s, 2 H), 7.96 (s, 1 H), 7.19 (d, J=2.4 Hz, 1 H), 6.77 (s, 2 H), 6.67 (dd, J=5.7, 2.5 Hz, 1 H), 3.84 (s, 3 H); MS (ESI) m/z: 269.1 (M+H+).

1. customThe mixture was degassed with argon
2. customsealed
3. additionThe mixture was diluted with EtOAc (75 mL) and water (40 mL)
4. filtrationwas filtered
5. customto collect an off-white solid
6. customThe organic phase was separated
7. washwashed with brine (40 mL)
8. customevaporated at reduced pressure
9. customto give additional off-white solid
10. customtriturated with EtOAc (15 mL) with sonication
11. filtrationThe solid was collected by filtration
12. washwashed with EtOAc (2×5 mL)
13. customdried under vacuum