反应详情

温度

90 °C

A mixture of 5-((6-chloropyrimidin-4-yl)oxy)pyridin-2-amine (0.50 g, 2.25 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.47 g, 2.25 mmol), and Cs2CO3 (1.46 g, 4.49 mmol) in 5:1 dioxane/water (6 mL) was sparged with Ar, treated with Pd(PPh3)4 (0.26 g, 0.23 mmol), sparged again with Ar and heated at 90° C. overnight. The mixture was cooled to RT, the solids removed via filtration, washed with dioxane and the filtrate concentrated to dryness. The residue was treated with water, extracted with EtOAc, washed with brine, dried over Na2SO4, and concentrated to dryness. The material was treated with EtOAc and the resulting solid collected via filtration to afford 5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-amine (0.41 g, 68%). 1H NMR (400 MHz, DMSO-d6): δ 8.60 (d, 1 H), 8.44 (s, 1 H), 8.12 (s, 1 H), 7.78 (d, 1 H), 7.28 (m, 2 H), 6.48 (d, 1 H), 5.94 (s, 2 H), 3.88 (s, 3 H); MS (ESI) m/z: 269.1 (M+H+).

1. customwas sparged with Ar
2. customsparged again with Ar
3. temperatureThe mixture was cooled to RT
4. customthe solids removed via filtration
5. washwashed with dioxane
6. concentrationthe filtrate concentrated to dryness
7. additionThe residue was treated with water
8. extractionextracted with EtOAc
9. washwashed with brine
10. dry with materialdried over Na2SO4
11. concentrationconcentrated to dryness
12. additionThe material was treated with EtOAc
13. filtrationthe resulting solid collected via filtration