反応 #1121776

反応方程式

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

thiophenol

sodium hydride

→

title compound 18b

収率 79.0%

2-Amino-5-phenyl-3-phenylthiopyrazine

収率 79.0%

溶媒

DMF

反応条件

後処理

1. 1
   温度the mixture refluxed for 20 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 (0.10 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).

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