Reaction #1121780

Reaction equation

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

phenol

sodium hydride

→

title compound 18q

Yield 62.0%

2-Amino-5-phenyl-3-phenoxypyrazine

Yield 62.0%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturethe mixture refluxed for 20 h
2. 2
   Temperaturecooled
3. 3
   Extractionextracted with EtOAc
4. 4
   WashThe organic layer was washed with water
5. 5
   Filtrationfiltered
6. 6
   Otherthe solvent removed under reduced pressure
7. 7
   Otherto get a crude that
8. 8
   Otherwas purified by flash chromatography

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+).

Source