Lithium hydroxide, monohydrate → 2-(2-Phenylpyrimidin-5-yl)thiazole-4-carboxylic acid

HRID 42314

반응식

HRID 42314 반응식
O.[OH-].[Li+].[C:4]1([C:10]2[N:15]=[CH:14][C:13]([C:16]3[S:17][CH:18]=[C:19]([C:21]([O:23]C(C)(C)C)=[O:22])[N:20]=3)=[CH:12][N:11]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C.O.CN(C=O)C>[C:4]1([C:10]2[N:15]=[CH:14][C:13]([C:16]3[S:17][CH:18]=[C:19]([C:21]([OH:23])=[O:22])[N:20]=3)=[CH:12][N:11]=2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 59252449Tert-butyl 2-(2-phenylpyrimidin-5-yl)thiazole-4-carboxylate

생성물 1

HCID 592524752-(2-Phenylpyrimidin-5-yl)thiazole-4-carboxylic acid수율 87%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

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.

후처리

  1. customEthanol was removed under reduced pressure
  2. additionthe solution diluted with water
  3. extractionsubsequently extracted with diethyl ether (2×30 mL)
  4. filtrationThe solid precipitate was filtered
  5. washwashed with water
  6. customdried under high vacuum

출처 및 근거

ORD 기록
ord-aeb70ef3f1d54c829010830539e88f70
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536185B2

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