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

HRID 473678Notes

Reaction equation

HRID 473678 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dc2e1948323847129c429ae114abdb48
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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