Reacción #1121777

Ecuación de reacción

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

cyclopentanethiol

sodium hydride

→

title compound 18n

Rendimiento 67.6%

2-Amino-5-phenyl-3-cyclopentylthiopyrazine

Rendimiento 67.6%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   Otroquenched with water
3. 3
   workup.ADDITIONThen EtOAc was added
4. 4
   Filtraciónfiltered
5. 5
   Otrothe solvent removed under reduced pressure
6. 6
   Otroto get a crude that
7. 7
   Otrowas purified by flash chromatography

Procedimiento

To a solution of cyclopentanethiol (0.18 g, 1.80 mmol) in dry acetonitrile (20 mL), sodium hydride (NaH) (0.04 g, 1.80 mmol) was added the resulting mixture was stirred for 15 min. After this time 2-amino-3-bromo-5-phenylpyrazine 17b (0.15 g, 0.6 mmol) was added and the mixture heated at 80° C. for 2 h, cooled and quenched with water. Then EtOAc was added and the organic layer was anidrified over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using dichloromethane-EtOAc (9:1 v/v) as eluent, to obtain 0.11 g of the title compound 18n as a yellow solid (mp 92-94° C., 67% yield). 1H-NMR (CDCl3): 1.68-1.83 (m, 6H), 2.28-2.31 (m, 2H), 4.21-4.28 (m, 1H), 4.93 (br s, 2H), 7.32-7.35 (m, 1H), 7.41-7.45 (m, 2H), 7.91-7.93 (m, 2H), 8.20 (s, 1H). MS (ESI): m/z 272 (Mile).

Fuente