反应详情

温度

20 °C

To a suspension of AlCl3 (736 mg, 5.44 mmol) in CHCl3 (5 mL) a solution of 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-2-methylpyrimidine (1.46 g, 4 mmol) in CHCl3 was added at 0° C., followed by Cl2CHOMe (0.4 mL, 4.4 mmol). The reaction was stirred at 0° C. for 2 h and at 20° C. for 16 h. Then an additional amount of Cl2CHOMe was added (0.2 mL, 2.2 mmol) and the reaction was continued for 26 h. The mixture was poured into ice/water (50 mL) and after quenching it was basified with 1 N NaOH, extracted with EtOAc (2×100 mL each) and the combined organic extracts were washed with water, brine, dried over (MgSO4) and stripped in vacuo. The residue was chromatographed on silica gel using 10% EtOAc/hexanes as eluent to give the product 4-(5,7-dichloro-2,3-dihydro-1H-indol-1-yl)-6-(1-ethylpropylamino)-5-formyl-2-methylpyrimidine (470 mg, 30% yield).

1. additionwas added at 0° C.
2. waitthe reaction was continued for 26 h
3. customafter quenching it
4. extractionextracted with EtOAc (2×100 mL each)
5. washthe combined organic extracts were washed with water, brine
6. dry with materialdried over (MgSO4)
7. customThe residue was chromatographed on silica gel using 10% EtOAc/hexanes as eluent