Reacción #1121775

Ecuación de reacción

2-amino-3-bromo-5-(4-methoxyphenyl)pyrazine

2-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

thiophenol

sodium hydride

→

title compound 18a

Rendimiento 70.0%

2-Amino-5-(4-methoxyphenyl)-3-phenylthiopyrazine

Rendimiento 70.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture refluxed for 6 h
2. 2
   Temperaturacooled
3. 3
   Extracciónextracted with EtOAc
4. 4
   LavadoThe organic layer was washed with water
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Otrothe solvent removed under reduced pressure
8. 8
   Otroto get a crude that
9. 9
   Otrowas purified by flash chromatography

Procedimiento

To a cooled solution of thiophenol (0.08 mL, 0.7 mmol) in dry DMF (10 mL), sodium hydride (NaH) (0.025 g, 1.00 mmol) was added and the resulting mixture was stirred for 15 min at 5-10° C. After this time 2-amino-3-bromo-5-(4-methoxyphenyl)pyrazine 17a (0.20 g, 0.71 mmol) was added and the mixture refluxed for 6 h, cooled and extracted with EtOAc. The organic layer was washed with water, dried over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using petroleum ether-EtOAc (65:45 v/v) as eluent, to obtain 0.15 g of the title compound 18a as an orange solid (mp 89-90° C., 70% yield). 1H-NMR (CDCl3): 3.81 (s, 3H), 4.90 (br s, 2H), 6.89 (d, J=8.7, 2H), 7.33-7.39 (m, 7.45-7.50 (m, 2H), 7.69 (d, J=8.7, 2H), 8.28 (s, 1H). MS (ESI): m/z 310 (M+H+).

Fuente