Reacción #1121780

Ecuación de reacción

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

phenol

sodium hydride

→

title compound 18q

Rendimiento 62.0%

2-Amino-5-phenyl-3-phenoxypyrazine

Rendimiento 62.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture refluxed for 20 h
2. 2
   Temperaturacooled
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent removed under reduced pressure
7. 7
   Otroto get a crude that
8. 8
   Otrowas purified by flash chromatography

Procedimiento

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+).

Fuente