Réaction #1121777

Équation de réaction

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

cyclopentanethiol

sodium hydride

→

title compound 18n

Rendement 67.6%

2-Amino-5-phenyl-3-cyclopentylthiopyrazine

Rendement 67.6%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Autrequenched with water
3. 3
   workup.ADDITIONThen EtOAc was added
4. 4
   Filtrationfiltered
5. 5
   Autrethe solvent removed under reduced pressure
6. 6
   Autreto get a crude that
7. 7
   Autrewas purified by flash chromatography

Mode opératoire

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).

Source