反应详情

温度

150 °C

To a solution of 1-(1-(5-amino-6-(methylamino)pyrimidin-4-yl)piperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one (50 mg, 0.14 mmol) in anhydrous DMA (5 mL) and diisopropylethylamine (0.5 mL) were added HATU (150 mg, 0.39 mmol), and pyrimidine-4-carboxylic acid (100 mg, 0.8 mmol). The reaction mixture was stirred for 1 h, and concentrated under reduced pressure. The resulting oil was dissolved in 10 mL of dichloromethane, and the solution was washed with 5 mL of water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the residue was dissolved in Acetic acid (2 mL). The reaction mixture was heated in a microwave reactor to 150° C. for 20 min, and concentrated under reduced pressure. The product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid) to give 3 mg of the title compound. 1H NMR (400 MHz, DMSO-d6): δ 10.85 (s, 1H), 9.34 (s, 1H), 8.96 (d, 1H), 8.36 (s, 1H), 8.27 (d, 1H), 7.21-7.14 (m, 1H), 6.93 (d, 3H), 4.64-4.52 (m, 1H), 4.18 (s, 3H), 2.37 (dd, 2H), 1.85 (t, 2H); MS (EI) for C23H21N9O: 428.4 (MH+).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe resulting oil was dissolved in 10 mL of dichloromethane
3. washthe solution was washed with 5 mL of water
4. dry with materialThe organic layer was dried over MgSO4
5. concentrationconcentrated under reduced pressure
6. dissolutionthe residue was dissolved in Acetic acid (2 mL)
7. concentrationconcentrated under reduced pressure
8. customThe product was purified by preparatory HPLC (reverse-phase, acetonitrile/water with 0.1% formic acid)