反应详情

To a solution of 1-(2-aminopyrimidin-4-yl)-6-bromo-2,3-dihydro-1H-1,3-benzodiazol-2-one (500 mg, 1.63 mmol) in DMF (10 ml) at 0° C. was added sodium hydride (60% oil suspension, 65.33 g, 1.63 mmol). The reaction mixture was allowed to warm to RT over 5 minutes before addition of iodomethane (0.1 ml, 1.63 mmol) and stirring for 30 minutes. The mixture was quenched by addition of water (5 mL), EtOAc was then added resulting in formation of a precipitate. The precipitate was collected by suction filtration. The filtrate was extracted with EtOAc (×2). The combined organic fractions were washed with water and dried (Na2SO4), filtered and concentrated in vacuo. Combining the extract residue and the precipitate gave the crude title compound (600 mg); 1H NMR (500 MHz, CDCl3) delta 3.23 (3H, s), 5.55 (2H, s), 6.72 (1H, d, J=8.3 Hz), 7.20-7.04 (1H, m), 7.42 (1H, d, J=5.7 Hz), 8.12 (1H, d, J=5.7 Hz), 8.39 (1H, d, J=1.8 Hz); LC-MS: m/z=+321.8 (M+H)+.

1. customThe mixture was quenched by addition of water (5 mL), EtOAc
2. additionwas then added
3. customresulting in formation of a precipitate
4. filtrationThe precipitate was collected by suction filtration
5. extractionThe filtrate was extracted with EtOAc (×2)
6. washThe combined organic fractions were washed with water
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo