Reacción #70592

Ecuación de reacción

lithium hydroxide monohydrate

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

→

title compound

Rendimiento 87.0%

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

Rendimiento 87.0%

Disolventes

DMF

ethanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroEthanol was removed under reduced pressure
2. 2
   workup.ADDITIONthe solution diluted with water
3. 3
   Extracciónsubsequently extracted with diethyl ether (2×30 mL)
4. 4
   FiltraciónThe solid precipitate was filtered
5. 5
   Lavadowashed with water
6. 6
   Otrodried under high vacuum

Procedimiento

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.

Fuente