반응 #70592

반응 방정식

lithium hydroxide monohydrate

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

→

title compound

수율 87.0%

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

수율 87.0%

용매

DMF

ethanol

water

반응 조건

후처리

1. 1
   기타Ethanol was removed under reduced pressure
2. 2
   workup.ADDITIONthe solution diluted with water
3. 3
   추출subsequently extracted with diethyl ether (2×30 mL)
4. 4
   여과The solid precipitate was filtered
5. 5
   세척washed with water
6. 6
   기타dried under high vacuum

실험 절차

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.

출처