Réaction #1121774

Équation de réaction

2-amino-5-(4-mcthoxyphenyl)pyrazinc

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

pyridine

bromine

→

17a

Rendement 70.0%

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

Rendement 70.0%

Solvants

chloroform

chloroform

Conditions de réaction

Traitement

1. 1
   Lavagethe reaction mixture was washed with water
2. 2
   Séchagethe organic layer dried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Autrethe solvent was removed under reduced pressure
5. 5
   AutreThe crude product was purified by flash chromatography

Mode opératoire

To a solution of 2-amino-5-(4-mcthoxyphenyl)pyrazinc 16a (0.35 g, 1.7 mmol) and pyridine (0.20 mL, 2.6 mmol) in chloroform (20 mL), bromine (Br2) (0.13 mL, 2.6 mmol) was added dropwise in chloroform (3 mL) at −10° C. After 6 h stirring at room temperature, the reaction mixture was washed with water, the organic layer dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography using dichloromethane-EtOAc (90:10 v/v) as eluent, to obtain 0.33 g of 17a as an brown solid (mp 166-170° C., 70% yield). 1H-NMR (CDCl3): 3.83 (s, 3H), 5.04 (br s, 2H), 6.92-6.96 (m, 2H), 7.76-7.80 (m, 2H), 8.31 (s, 1H). GC-MS (EI): m/z 279,281 (M1, 100).

Source