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Sodium hydride → 2-Methyl-8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-quinoxaline

HRID 858994
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HRID 858994 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH3:18][C:19]1[CH:20]=[N:21][C:22]2[CH:23]=[CH:24][CH:25]=[C:26]([OH:29])[C:27]=2[N:28]=1.[H-].[Na+]>CN(C=O)C>[CH3:18][C:19]1[CH:20]=[N:21][C:22]2[C:27](=[C:26]([O:29][C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=4)[N:5]=[CH:4][N:3]=3)[CH:25]=[CH:24][CH:23]=2)[N:28]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidineHCID 1354072263-Methylquinoxalin-5-ol

생성물 1

HCID 100454262-Methyl-8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-quinoxaline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To a mixture of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (0.20 g, 0.77 mmol) and 3-methyl-quinoxalin-5-ol (0.14 g, 0.85 mmol, prepared according to J. Med. Chem. 1988, 41, 4062–4079.) in DMF (3 mL) was added sodium hydride (0.040 g, 1.0 mmol, 60% dispersion in mineral oil, Aldrich). The reaction was heated at 60° C. for 24 h, allowed to cool to room temperature and partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (4×). The combined organic layers were dried over MgSO4, filtered and the solvent was removed in vacuum. The residue was purified by flash chromatography (0→75% EtOAc/hexanes) to give the title compound as an ivory powder. Mp: 139–141° C., MS (ESI, pos. ion) m/z: 383 (M+1).

후처리

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc and H2O
  3. extractionThe aqueous layer was extracted with EtOAc (4×)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuum
  7. customThe residue was purified by flash chromatography (0→75% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-daf2b094ed864113b059aaaf3fadcdeb
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07148221B2

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