Phenol → HCID 66848872, compound

HRID 1034598Notes

Reaction equation

HRID 1034598 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH2:10][C:11]1[C:16](Br)=[N:15][C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][N:12]=1>CN(C=O)C>[NH2:10][C:11]1[C:16]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:15][C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 124535523-Bromo-5-phenylpyrazin-2-amine

Product 1

HCID 66848872HCID 66848872, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
7.5 °C

Procedure

To a cooled solution of phenol (0.07 mL, 0.80 mmol) in dry DMF (5 mL), sodium hydride (NaH) (0.02 g, 0.80 mmol) was added and the resulting mixture was cooled at 5-10° C. and stirred for 15 min. After this time 2-amino-3-bromo-5-phenylpyrazine 17b (0.25 g, 1.00 mmol) was added and the mixture refluxed for 20 h, cooled and extracted with EtOAc. The organic layer was washed with water, anidrified over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using dichloromethane-EtOAc (70:30 v/v) as eluent, to obtain 0.13 g of the title compound 18q as a pink solid (mp 129-131° C., 62% yield). 1H-NMR (CDCh): 5.04 (br s, 2H), 7.28-7.43 (m, 8H), 7.69-7.73 (m, 2H), 8.18 (s, 1H). MS (ESI): m/z 264 (M+H+).

Workup

  1. temperaturethe mixture refluxed for 20 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customto get a crude that
  8. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-96b72f5809594523be775b711b127582
Source dataset
uspto-grants-2013_10
Patent number
US08546147B2

Reaction notes

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