Réaction #1121776

Équation de réaction

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

thiophenol

sodium hydride

→

title compound 18b

Rendement 79.0%

2-Amino-5-phenyl-3-phenylthiopyrazine

Rendement 79.0%

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
   Séchagedried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Autrethe solvent removed under reduced pressure
8. 8
   Autreto get a crude that
9. 9
   Autrewas purified by flash chromatography

Mode opératoire

To a cooled solution of thiophenol (0.10 mL, 1.00 mmol) in dry DMF (10 mL), sodium hydride (NaH) (0.025 g, 1.00 mmol) was added the resulting mixture was stirred for 15 min at 5-10° C. 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, 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 (60:40 v/v) as eluent, to obtain 0.22 g of the title compound 18b as a brown solid (mp 109-112° C., 79% yield). 1H-NMR (CDCl3): 4.92 (br s, 2H), 7.29-7.50 (m, 8H), 7.74-7.77 (m, 2H), 8.35 (s, 1H). MS (ESI): m/z 280 (M+H1).

Source