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

HRID 2055943
ノート
印刷プレビュー

反応式

HRID 2055943 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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 x). 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).

後処理

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc and H2O
  3. extractionThe aqueous layer was extracted with EtOAc (4 x)
  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)

出典と根拠

ORDレコード
ord-993104766a4f44639d86bfecbfdfff1b
出典データセット
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07332511B2

反応ノート

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