反应详情

温度

140 °C

A glass microwave reaction vessel was charged with 5-iodo-N4-(6-methoxypyridin-3-yl)-N2,N2-dimethylpyrimidine-2,4-diamine (98 mg, 0.264 mmol), 2-methyl-4-(methylthio)-6-(tributylstannyl)-1,3,5-triazine (114 mg, 0.264 mmol), cesium fluoride (80 mg, 0.528 mmol), copper(I) iodide (10 mg, 0.053 mmol), tetrakis(triphenylphosphine)palladium(0) (30.5 mg, 0.026 mmol) and dioxane (2 mL). The reaction mixture was stirred and heated in a Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 140° C. for 30 min. The reaction mixture was diluted with water (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (10 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as an orange solid. The crude product was purified by silica gel chromatography eluting with 60% EtOAc/hexanes to give N4-(6-methoxypyridin-3-yl)-N2,N2-dimethyl-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)pyrimidine-2,4-diamine (32 mg, 0.083 mmol, 31.5% yield). 1H NMR (300 MHz, CDCl3) δ 11.66 (s, 1H); 9.43 (s, 1H); 8.42 (s, 1H); 8.05 (dd, J=8.70, 2.27 Hz, 1H); 6.77 (d, J=8.92 Hz, 1H); 3.95 (s, 3H); 3.25 (s, 6H); 2.59 (s, 3H); 2.57 (s, 3H). m/z (ESI, +ve ion) 385.1 (M+H)+.

1. customA glass microwave reaction vessel
2. extractionextracted with EtOAc (2×30 mL)
3. extractionThe organic extract
4. washwas washed with saturated NaCl (10 mL)
5. dry with materialdried over Na2SO4
6. filtrationThe solution was filtered
7. concentrationconcentrated in vacuo
8. customto give the crude material as an orange solid
9. customThe crude product was purified by silica gel chromatography
10. washeluting with 60% EtOAc/hexanes