反応 #1121775

反応方程式

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

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

thiophenol

sodium hydride

→

title compound 18a

収率 70.0%

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

収率 70.0%

溶媒

DMF

反応条件

後処理

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

実験手順

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+).

出典