反应详情

To a solution of 4-chloro-6,7-dimethoxy-2-methylquinazoline (From example 24; 700 mg, 2.93 mmol) in isopropanol (20 mL) was added 4-amino-5-methylselenophene-2-carboxylate (1.3 g, 5.8 mmol) at rt and the mixture was stirred at rt for 16 h. The mixture was poured into ice cooled water and stirred for 10 min. The solution was extracted with EtOAc (3×100 mL) and the combined layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform-methanol (98:2) as eluents to give the product (700 mg, 57%) as a brown color solid, mp 200-204° C. 1H NMR (400 MHz, CDCl3): δ 8.18 (1H, s), 7.19 (1H, s), 7.00 (1H, s), 3.98 (3H, s), 3.92 (3H, s), 3.85 (3H, s), 2.58 (3H, s), 2.46 (3H, s); 13C NMR (100 MHz, CDCl3): δ 163.5, 162.8, 156.9, 154.8, 148.7, 148.2, 144.0, 135.3, 135.1, 131.8, 107.3, 106.4, 99.8, 56.2, 56.1, 52.2, 26.2, 15.5; LC-MS (positive ion mode): m/z 420, 422 (M+H)+.

1. additionThe mixture was poured into ice
2. stirringstirred for 10 min
3. extractionThe solution was extracted with EtOAc (3×100 mL)
4. washthe combined layer was washed with water, brine
5. dry with materialdried over sodium sulfate
6. filtrationThe solution was filtered
7. customevaporated the solvent
8. customThe residue was chromatographed over silica gel column