反应详情

温度

155 °C

A mixture of 2-amino-4,6-dimethylbenzamide (0.2 g, 1.22 mmol), 4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-3,5-dimethyl-benzaldehyde (0.376 g, 1.22 mmol), sodium hydrogensulfite (0.22 g, 1.22 mmol) and p-toluenesulfonic acid (0.116 g, 0.61 mmol) in N,N-dimethyl acetamide (10 mL) was stirred at 155° C. for 14 h. The reaction mixture was cooled to room temperature and diluted with water (50 mL). The solid crashed out and was collected by filtration to afford impure product. The solid was re-dissolved in THF (30 mL) and mixed with TBAF in THF (5 mL, 5 mmol). The reaction mixture was stirred at room temperature for 14 h and concentrated using a rotary evaporator to afford an oily residue. Further purification by column (SiO2, EtOAc/DCM/MeOH=12:4:1) yielded an off-white solid. This solid was diluted with MeOH (10 mL) to make a slurry. The solid was collected by filtration and washed with MeOH to afford 2-(4-(2-hydroxyethoxy)-3,5-dimethylphenyl)-5,7-dimethylquinazolin-4(3H)-one (98 mg, 24%) as a white solid. Selected data: MS (ES) m/z: 339.10; MP 259.6-261.2° C.

1. temperatureThe reaction mixture was cooled to room temperature
2. filtrationwas collected by filtration
3. customto afford impure product
4. stirringThe reaction mixture was stirred at room temperature for 14 h
5. concentrationconcentrated
6. customa rotary evaporator
7. customto afford an oily residue
8. customFurther purification by column (SiO2, EtOAc/DCM/MeOH=12:4:1)
9. customyielded an off-white solid
10. filtrationThe solid was collected by filtration
11. washwashed with MeOH