反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
To a solution of methyl 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (INTERMEDIATE 27)(2 g, 3.63 mmol) in anhydrous THF at 0° C. was added lithium aluminum hydride (1.0M in THF, 4.7 mL, 4.73 mmol) slowly. The reaction was stirred at 0° C. for 40 min, quenched with water slowly and diluted with methylene chloride. The mixture was filtered through celite and rinsed with methylene chloride. Removal of the solvent and subsequent purification by flash chromatography using 20% of acetone in hexane as eluent provided the 5-bromo-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid. 1H NMR (CDCl3, 500 MHz): δ 3.83 (s, 3H), 4.49 (s, 2H), 4.50 (s, 2H), 4.69 (s, 2H), 5.98 (s, 1H), 6.92 (d, 2H, J=8.5 Hz), 7.23 (s, 1H), 7.36 (m, 3H), 7.52 (d, 2H, J=8.0 Hz). MS (API-ES+): 523 (M+H).
WORKUP
后处理
- customquenched with water slowly
- additiondiluted with methylene chloride
- filtrationThe mixture was filtered through celite
- washrinsed with methylene chloride
- customRemoval of the solvent and subsequent purification by flash chromatography