反应详情

温度

100 °C

To a 20 mL microwave reaction tube was added 4-chloro-6-methyl-1,3,5-triazin-2-amine (Example 9, 1.02 g, 7.05 mmol), 2-fluoro-5-methoxypyridin-3-ylboronic acid (1.67 g, 9.77 mmol), Am-Phos (Aldrich, 0.255 g, 0.360 mmol) and potassium acetate (Aldrich, 2.11 g, 21.5 mmol) in EtOH (10 mL) and water (1 mL). The mixture was degassed by bubbling argon through for 5 min. The tube was heated in a microwave reactor (Biotage) at 100° C. for 20 min. The reaction mixture was partitioned between water (200 mL) and EtOAc (200 mL). Layers were separated and insoluble material was collected (precipitate 1). The aqueous phase was further extracted with 10% isopropanol in chloroform (3×100 mL). Each organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. Upon addition of DCM to the crude product, precipitate came out and the solid was collected via filtration. The first precipitate (precipitate 1) and the solid from extraction were all desired product (1.17 g, 70.3%). 1H NMR (400 MHz, CDCl3) δ ppm 8.08 (dd, J=7.53, 3.23 Hz, 1H) 7.97 (dd, J=3.03, 1.86 Hz, 1H) 5.47 (br. s., 2H) 3.92 (s, 3H) 2.54 (s, 3H). m/z (ESI, positive ion): 236.0 (M+H)+.

1. customThe mixture was degassed
2. customby bubbling argon through for 5 min
3. customThe reaction mixture was partitioned between water (200 mL) and EtOAc (200 mL)
4. customLayers were separated
5. custominsoluble material was collected (precipitate 1)
6. extractionThe aqueous phase was further extracted with 10% isopropanol in chloroform (3×100 mL)
7. dry with materialEach organic phase was dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. additionUpon addition of DCM to the crude product, precipitate
11. filtrationthe solid was collected via filtration
12. extractionThe first precipitate (precipitate 1) and the solid from extraction