Reaction #70592

Reaction equation

lithium hydroxide monohydrate

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

→

title compound

Yield 87.0%

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

Yield 87.0%

Solvents

DMF

ethanol

water

Conditions

Workup

1. 1
   OtherEthanol was removed under reduced pressure
2. 2
   workup.ADDITIONthe solution diluted with water
3. 3
   Extractionsubsequently extracted with diethyl ether (2×30 mL)
4. 4
   FiltrationThe solid precipitate was filtered
5. 5
   Washwashed with water
6. 6
   Otherdried under high vacuum

Procedure

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.

Source