Water → HCID 86698303, compound

Participants

Reaction Steps

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)+.

Provenance & Evidence