反应详情

温度

100 °C

A glass microwave reaction vessel was charged with 4-(3-chloropyridin-4-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (32 mg, 0.069 mmol), 5-amino-2-methoxypyridine (0.017 mL, 0.139 mmol), Brett precatalyst ((SP-4-4)-[2-[2-(amino-κN)ethyl]phenyl-κC]chloro[dicyclohexyl[3,6-dimethoxy-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]phosphine-κP]palladium) (2 mg) and sodium 2-methylpropan-2-olate (16.64 mg, 0.173 mmol) and dioxane (1 mL). The reaction mixture was stirred and heated in an oil bath at 100° C. for 16 h. The reaction mixture was diluted with saturated NH4Cl (10 mL) and extracted with EtOAc (2×20 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as orange oil. The crude product was purified by silica gel chromatography eluting with 20% THF/CH2Cl2 to give N,N-bis(4-methoxybenzyl)-4-(3-(6-methoxypyridin-3-ylamino)pyridin-4-yl)-6-methyl-1,3,5-triazin-2-amine (9 mg, 0.016 mmol, 24% yield). 1H NMR (300 MHz, CDCl3) δ 10.32 (s, 1H); 8.49-8.68 (m, 1H); 8.33 (s, 1H); 8.24 (d, J=5.12 Hz, 2H); 8.03 (d, J=5.12 Hz, 2H); 7.95 (d, J=1.61 Hz, 1H); 7.38 (dd, J=8.70, 2.41 Hz, 2H); 7.21 (d, J=8.33 Hz, 2H); 7.14 (d, J=8.33 Hz, 2H); 6.98 (s, 1H); 6.87 (d, J=8.33 Hz, 2H); 6.79 (d, J=8.33 Hz, 2H); 6.72 (d, J=8.77 Hz, 1H); 4.86 (s, 2H); 4.79 (s, 2H); 3.81 (s, 3H); 3.76 (s, 3H); 2.56 (s, 3H). m/z (ESI, +ve ion) 550.0 (M+H)+.

1. customA glass microwave reaction vessel
2. extractionextracted with EtOAc (2×20 mL)
3. extractionThe organic extract
4. washwas washed with saturated NaCl (5 mL)
5. dry with materialdried over Na2SO4
6. filtrationThe solution was filtered
7. concentrationconcentrated in vacuo
8. customto give the crude material as orange oil
9. customThe crude product was purified by silica gel chromatography
10. washeluting with 20% THF/CH2Cl2