反応 #1121780

反応方程式

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

phenol

sodium hydride

→

title compound 18q

収率 62.0%

2-Amino-5-phenyl-3-phenoxypyrazine

収率 62.0%

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
   ろ過filtered
6. 6
   その他the solvent removed under reduced pressure
7. 7
   その他to get a crude that
8. 8
   その他was purified by flash chromatography

実験手順

To a cooled solution of phenol (0.07 mL, 0.80 mmol) in dry DMF (5 mL), sodium hydride (NaH) (0.02 g, 0.80 mmol) was added and the resulting mixture was cooled at 5-10° C. and stirred for 15 min. 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, anidrified over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using dichloromethane-EtOAc (70:30 v/v) as eluent, to obtain 0.13 g of the title compound 18q as a pink solid (mp 129-131° C., 62% yield). 1H-NMR (CDCh): 5.04 (br s, 2H), 7.28-7.43 (m, 8H), 7.69-7.73 (m, 2H), 8.18 (s, 1H). MS (ESI): m/z 264 (M+H+).

出典