反应 #70592

反应方程式

lithium hydroxide monohydrate

tert-butyl 2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxylate

→

title compound

收率 87.0%

2-(2-Phenylpyrimidin-5-yl)thiazole-4-carboxylic acid

收率 87.0%

溶剂

DMF

ethanol

water

反应条件

后处理

1. 1
   其他Ethanol was removed under reduced pressure
2. 2
   workup.ADDITIONthe solution diluted with water
3. 3
   萃取subsequently extracted with diethyl ether (2×30 mL)
4. 4
   过滤The solid precipitate was filtered
5. 5
   洗涤washed with water
6. 6
   其他dried under high vacuum

实验过程

To a solution consisting of lithium hydroxide monohydrate (0.38 g, 9.0 mmol) dissolved in ethanol (20 mL)/water (10 mL) was added tert-butyl 2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxylate (Example 62, 705 mg, 3.0 mmol) in dry DMF (11 mL) and the mixture stirred at room temperature for 18 hours. Ethanol was removed under reduced pressure and the solution diluted with water and subsequently extracted with diethyl ether (2×30 mL). The aqueous phase was acidified with 2 N hydrochloric acid to pH2. The solid precipitate was filtered, washed with water and dried under high vacuum to give the title compound as an off-white solid (371 mg, 87% yield); Rf 0.15 with 9:1 v/v dichloromethane-methanol; 1H-NMR (300 MHz; DMSO-d6) δ 9.39 (s, 2H), 8.63 (s, 1H), 8.44 (dd, 2H), 7.55 (m, 3H); MS (ESI+) m/z 284 (M+1); H-PGDS FPBA IC50: 1.1 μM.

来源