2-Fluorophenol → 5-(2-Fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine

HRID 81359

반응식

HRID 81359 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].Cl[C:12]1[N:13]=[CH:14][C:15]2[N:20]=[C:19]([C:21]3[CH:26]=[C:25]([CH3:27])[C:24]([O:28][CH3:29])=[C:23]([CH3:30])[CH:22]=3)[O:18][C:16]=2[N:17]=1>CC(N(C)C)=O>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:12]1[N:13]=[CH:14][C:15]2[N:20]=[C:19]([C:21]3[CH:22]=[C:23]([CH3:30])[C:24]([O:28][CH3:29])=[C:25]([CH3:27])[CH:26]=3)[O:18][C:16]=2[N:17]=1

참가 물질

5

반응물 3

HCID 97072-FluorophenolHCID 24758Sodium hydrideHCID 866759545-Chloro-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[5,4-d]pyrimidine

생성물 1

HCID 533113735-(2-Fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

149 mg of sodium hydride were added under an argon atmosphere to a solution of 418 mg of 2-fluoro-phenol in 15 ml dimethylacetamide. After stirring for 30 min at room temperature a solution of 900 mg of 5-chloro-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine in 20 ml dimethylacetamide was added slowly. The mixture was allowed to stir for 1.5 h at room temperature. Upon consumption of the starting oxazolo[5,4-d]pyrimidine an aqueous solution of citric acid (100 g/l) was added until the pH was neutral. The aqueous layer was extracted twice with 15 ml of ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvents were removed in vacuo. The title compound was isolated by silica gel chromatography (heptane/ethyl acetate gradient) as a white solid. Yield: 820 mg.

후처리

  1. additionwas added slowly
  2. customUpon consumption of the starting oxazolo[5,4-d]pyrimidine an aqueous solution of citric acid (100 g/l)
  3. additionwas added until the pH
  4. extractionThe aqueous layer was extracted twice with 15 ml of ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-b0a87601989c458e9eb5b0a7ac85ad9f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846690B2

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