反应详情

A mixture of 7-acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one (1.69 g, 7.2 mmol), thionyl chloride (50 ml) and DMF (3 drops) was heated at reflux for 2 hours. The excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate solution. The organic phase was separated, dried (MgSO4) and the solvent removed by evaporation. 5-Benzyloxy-2-fluoro-4-methylaniline (1.8 g, 7.8 mmol) in isopropanol (50 ml) was added to the residue and the mixture heated at reflux for 2 hours. The mixture was allowed to cool, hexane added and the precipitated product collected by filtration to give 7-acetoxy-4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline (1.34 g, 43%).

1. temperaturewas heated
2. temperatureat reflux for 2 hours
3. customThe excess thionyl chloride was removed by evaporation
4. customthe residue azeotroped with toluene
5. customThe residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate solution
6. customThe organic phase was separated
7. dry with materialdried (MgSO4)
8. customthe solvent removed by evaporation
9. temperaturethe mixture heated
10. temperatureat reflux for 2 hours
11. temperatureto cool
12. filtrationthe precipitated product collected by filtration