反应详情

A stirred mixture of (4-benzyloxy-phenyl)-(6-ethynylquinazolin-4-yl)-amine (0.20 g, 0.57 mmol), nitroethane (0.20 g, 2.7 mmol), phenylisocyanate (0.15 ml, 0.164 g, 1.38 mmol), and triethylamine (3 drops) in a mixture of ethyl acetate (10 ml) and dichloromethane (5 ml) was heated at reflux for 18 hours. After cooling the mixture was filtered to remove solid, and the concentrated filtrate was purified by silica gel chromatography, eluting with 50% ethyl acetate/i-hexane. After concentration of the appropriate fractions, the material obtained was treated with methanolic HCl, the solvent was removed in vacuo and the residue was triturated with ether to give the title compound as a yellow solid (0.027 g, 0.061 mmol, 11%); δH [2H6]DMSO 12.0 (1H,s), 9.55 (1H,s), 8.91 (1H,s), 8.48 (1H,d), 8.03 (1H,d), 7.68 (2H,d), 7.32-7.55 (5H,m), 7.22 (1H,s), 7.15 (2H,d), 5.18 (2H,s), 2.35 (3H,s); m/z (M+1+) 409.

1. temperaturewas heated
2. temperatureat reflux for 18 hours
3. temperatureAfter cooling the mixture
4. filtrationwas filtered
5. customto remove solid
6. customthe concentrated filtrate was purified by silica gel chromatography
7. washeluting with 50% ethyl acetate/i-hexane
8. customAfter concentration of the appropriate fractions, the material obtained
9. customthe solvent was removed in vacuo
10. customthe residue was triturated with ether