反应详情

Phosphorus oxytrichloride (0.1 ml) was added to a mixture of 6-methoxy-7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one (81 mg, 0.29 mmol) and N,N-dimethylaniline (0.1 ml) in toluene (5 ml), and the mixture heated at reflux for 1 hour. The volatiles were removed by evaporation and the residue partitioned between methylene chloride and aqueous ammonia. The organic extract was separated, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by chromatography on silica eluting with ethyl acetate progressing through increasingly polar mixtures to methanol/methylene chloride (1/9) to give 4-chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline (40 mg, 41%). 1H NMR Spectrum: (DMSOd6) 4.04(s, 3H); 5.47(s, 2H); 7.46(s, 1H); 7.50(d, 2H); 7.53(s, 1H); 8.60(d, 2H); 8.85(s, 1H) MS-ESI: 302 [MH]+

1. temperaturethe mixture heated
2. temperatureat reflux for 1 hour
3. customThe volatiles were removed by evaporation
4. customthe residue partitioned between methylene chloride and aqueous ammonia
5. extractionThe organic extract
6. customwas separated
7. dry with materialdried (MgSO4)
8. customthe solvent removed by evaporation
9. customThe residue was purified by chromatography on silica eluting with ethyl acetate progressing
10. temperaturethrough increasingly polar mixtures to methanol/methylene chloride (1/9)