Sodium ethoxide → 7-Benzyl-2-(4-methylbenzyl)-3,5,6,7,8,9-hexahydro-4H-pyrimido[4,5-d]azepin-4-one

反応式

Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[NH:12])[NH2:11])=[CH:5][CH:4]=1.Cl.[CH2:14]([N:21]1[CH2:27][CH2:26][C:25](=O)[CH:24]([C:29](OCC)=[O:30])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O-]CC.[Na+]>>[CH2:14]([N:21]1[CH2:22][CH2:23][C:24]2[C:29](=[O:30])[NH:12][C:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([CH3:2])=[CH:8][CH:7]=3)=[N:11][C:25]=2[CH2:26][CH2:27]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

反応物 3

HCID 2723922Sodium ethoxide

HCID 134308192-(4-Methylphenyl)ethanimidamide hydrochloride

HCID 67097548Ethyl 1-benzyl-5-oxoazepane-4-carboxylate hydrochloride

生成物 1

HCID 1360580937-Benzyl-2-(4-methylbenzyl)-3,5,6,7,8,9-hexahydro-4H-pyrimido[4,5-d]azepin-4-one収率 43%

実験手順

Under nitrogen, 2-(4-methylphenyl)ethanimidamide hydrochloride (360 mg, 1.95 mmol) and ethyl 1-benzyl-5-oxoazepane-4-carboxylate hydrochloride (500 mg, 1.61 mmol) were added to a freshly-prepared solution of sodium ethoxide (from sodium (120 mg, 5.22 mmol) dissolved in ethanol (15 ml)) and the mixture refluxed overnight. The reaction mixture was concentrated in vacuo and the residue treated with water. The mixture was acidified with 2M HCl solution, then rebasified using saturated aqueous NaHCO3 solution and extracted with dichloromethane. The dichloromethane extract was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by purified by column chromatography on silica gel, eluting with DCM:MeOH, 98:2 to 94:6, to afford the title compound as a solid in 43% yield, 250 mg.