Réaction #1121780

Équation de réaction

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

phenol

sodium hydride

→

title compound 18q

Rendement 62.0%

2-Amino-5-phenyl-3-phenoxypyrazine

Rendement 62.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températurethe mixture refluxed for 20 h
2. 2
   Températurecooled
3. 3
   Extractionextracted with EtOAc
4. 4
   LavageThe organic layer was washed with water
5. 5
   Filtrationfiltered
6. 6
   Autrethe solvent removed under reduced pressure
7. 7
   Autreto get a crude that
8. 8
   Autrewas purified by flash chromatography

Mode opératoire

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