Hydrochloric Acid → (4-Benzyloxy-phenyl)-(-6-(3-methylisoxazol-5-yl)-quinazolin-4-yl)-amine hydrochloride

Participants

Reaction Steps

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.

Provenance & Evidence