反応 #70592

反応方程式

lithium hydroxide monohydrate

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

→

title compound

収率 87.0%

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

収率 87.0%

溶媒

DMF

ethanol

water

反応条件

後処理

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

実験手順

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.

出典