反应详情

A mixture of 10% Pd/C (0.200 g, 0.188 mmol) and N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-propen-1-ylamino)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.200 g, 0.507 mmol) was suspended in ethanol (10 mL) and stirred. Added next was methanesulfonic acid (0.033 mL, 0.507 mmol), and the stirring contents were heated at reflux for 2 h. After cooling to room temperature, the reaction mixture was diluted with DCM and filtered through Celite. The filter pad was washed with 10% MeOH/DCM. The filtrate was pre-adsorped onto silica gel, and the crude product purified by silica gel chromatography (dry loaded, eluent: gradient of 5-80% Dichloromethane/Chloroform containing 10% 2M Ammonia (in methanol)). The collected product was dried in vacuum oven at 45° C. overnight. The final product was collected as 0.065 g (36%). LCMS E-S (M+H)=355.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.40 (d, J=6.82 Hz, 6H), 2.12 (s, 3H), 2.21 (s, 3H), 4.31 (d, J=5.05 Hz, 2H), 4.85-5.00 (m, 1H), 5.89 (s, 1H), 6.49-6.68 (m, 3H), 7.85 (s, 1H), 8.46 (t, J=5.05 Hz, 1H), 11.54 (br. s., 1H).

1. additionAdded next
2. temperaturethe stirring contents were heated
3. temperatureat reflux for 2 h
4. filtrationfiltered through Celite
5. washThe filter pad was washed with 10% MeOH/DCM
6. customthe crude product purified by silica gel chromatography (dry loaded, eluent: gradient of 5-80% Dichloromethane/Chloroform containing 10% 2M Ammonia (in methanol))
7. customThe collected product was dried in vacuum oven at 45° C. overnight
8. customThe final product was collected as 0.065 g (36%)