4-Aminophenol → 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline

HRID 473678ノート

反応式

HRID 473678 の反応式
F[C:2]1[C:7]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[O:11]1[CH2:12][CH2:13][CH:8]([C:7]2[C:2]([O:21][C:18]3[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=3)=[N:3][CH:4]=[CH:5][N:6]=2)[CH2:9][CH2:10]1

参加物

6

反応物 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 593512282-fluoro-3-(Tetrahydro-2H-pyran-4-yl)pyrazine

生成物 1

HCID 593511704-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To a round-bottomed flask was added 2-fluoro-3-(tetrahydro-2H-pyran-4-yl)pyrazine (1.1147 g, 6.12 mmol), 4-aminophenol (0.801 g, 7.34 mmol), and cesium carbonate (5.98 g, 18.35 mmol) in DMSO (20.39 mL) at 110° C. to stir. The reaction mixture was diluted with water and extracted with dichloromethane. The organic extract was washed with water, brine, dried with magnesium sulfate, filtered, and concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide 4-(3-(tetrahydro-2H-pyran-4-yl)pyrazin-2-yloxy)aniline. MS (ESI, pos. ion) m/z: 272.1.

後処理

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed

出典と根拠

ORDレコード
ord-dc2e1948323847129c429ae114abdb48
出典データセット
uspto-grants-2014_01
特許番号
US08637500B2

反応ノート

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