Réaction #1121775

Équation de réaction

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

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

thiophenol

sodium hydride

→

title compound 18a

Rendement 70.0%

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

Rendement 70.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températurethe mixture refluxed for 6 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 (0.08 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+).

Source