反应详情

A solution of tert-butyl 5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-ylamino)pyridin-2-ylcarbamate (0.827 g, 1.24 mmol) and TFA (5.0 mL, 64.9 mmol) in DCM (10 mL) was stirred at rt for 1.5 h. Toluene (3 mL) was added and the mixture was concentrated in vacuo. Saturated aqueous sodium bicarbonate (50 mL) was added carefully. The aqueous phase was extracted with 25% iPrOH in CHCl3+1% NH4OH (2×50 mL). The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo to give N5-(3-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-5-chloropyridin-2-yl)pyridine-2,5-diamine (0.664 g, 94% yield) as a bright orange solid. 1H NMR (300 MHz, CDCl3) δ 11.46 (s, 1H); 8.72 (d, J=2.48 Hz, 1H); 8.17 (d, J=2.34 Hz, 1H); 8.06-8.13 (m, 1H); 7.64-7.75 (m, 1H); 7.18 (dd, J=12.57, 8.48 Hz, 4H); 6.86 (t, J=7.89 Hz, 4H); 6.49 (d, J=8.77 Hz, 1H); 4.83 (d, J=15.05 Hz, 4H); 4.31 (br. s., 2H); 3.80 (d, J=5.85 Hz, 6H); 2.56 (s, 3H). m/z (ESI, +ve ion) 569.2 (M+H)+.

1. concentrationthe mixture was concentrated in vacuo
2. additionSaturated aqueous sodium bicarbonate (50 mL) was added carefully
3. extractionThe aqueous phase was extracted with 25% iPrOH in CHCl3+1% NH4OH (2×50 mL)
4. dry with materialThe combined organic phases were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo