反应 #1121775

反应方程式

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

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

thiophenol

sodium hydride

→

title compound 18a

收率 70.0%

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

收率 70.0%

溶剂

DMF

反应条件

后处理

1. 1
   温度the mixture refluxed for 6 h
2. 2
   温度cooled
3. 3
   萃取extracted with EtOAc
4. 4
   洗涤The organic layer was washed with water
5. 5
   干燥dried over Na2SO4
6. 6
   过滤filtered
7. 7
   其他the solvent removed under reduced pressure
8. 8
   其他to get a crude that
9. 9
   其他was purified by flash chromatography

实验过程

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+).

来源