Реакция #1121777

Уравнение реакции

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

cyclopentanethiol

sodium hydride

→

title compound 18n

Выход 67.6%

2-Amino-5-phenyl-3-cyclopentylthiopyrazine

Выход 67.6%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Температураcooled
2. 2
   Другоеquenched with water
3. 3
   workup.ADDITIONThen EtOAc was added
4. 4
   Фильтрацияfiltered
5. 5
   Другоеthe solvent removed under reduced pressure
6. 6
   Другоеto get a crude that
7. 7
   Другоеwas purified by flash chromatography

Методика

To a solution of cyclopentanethiol (0.18 g, 1.80 mmol) in dry acetonitrile (20 mL), sodium hydride (NaH) (0.04 g, 1.80 mmol) was added the resulting mixture was stirred for 15 min. After this time 2-amino-3-bromo-5-phenylpyrazine 17b (0.15 g, 0.6 mmol) was added and the mixture heated at 80° C. for 2 h, cooled and quenched with water. Then EtOAc was added and the organic layer was anidrified over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using dichloromethane-EtOAc (9:1 v/v) as eluent, to obtain 0.11 g of the title compound 18n as a yellow solid (mp 92-94° C., 67% yield). 1H-NMR (CDCl3): 1.68-1.83 (m, 6H), 2.28-2.31 (m, 2H), 4.21-4.28 (m, 1H), 4.93 (br s, 2H), 7.32-7.35 (m, 1H), 7.41-7.45 (m, 2H), 7.91-7.93 (m, 2H), 8.20 (s, 1H). MS (ESI): m/z 272 (Mile).

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