Реакция #1121776

Уравнение реакции

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

thiophenol

sodium hydride

→

title compound 18b

Выход 79.0%

2-Amino-5-phenyl-3-phenylthiopyrazine

Выход 79.0%

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
   Сушкаdried over Na2SO4
6. 6
   Фильтрацияfiltered
7. 7
   Другоеthe solvent removed under reduced pressure
8. 8
   Другоеto get a crude that
9. 9
   Другоеwas purified by flash chromatography

Методика

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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