Реакция #1121780

Уравнение реакции

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

phenol

sodium hydride

→

title compound 18q

Выход 62.0%

2-Amino-5-phenyl-3-phenoxypyrazine

Выход 62.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураthe mixture refluxed for 20 h
2. 2
   Температураcooled
3. 3
   Экстракцияextracted with EtOAc
4. 4
   ПромывкаThe organic layer was washed with water
5. 5
   Фильтрацияfiltered
6. 6
   Другоеthe solvent removed under reduced pressure
7. 7
   Другоеto get a crude that
8. 8
   Другоеwas purified by flash chromatography

Методика

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+).

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