Реакция #1121778

Уравнение реакции

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

1-adamantanethiol

sodium hydride

→

title compound 18o

Выход 62.0%

2-Amino-5-phenyl-3-adamantylthiopyrazine

Выход 62.0%

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 1-adamantanethiol (0.07 g, 0.4 mmol) in dry acetonitrile (10 mL), sodium hydride (NaH) (9 mg, 0.4 mmol) was added and the resulting mixture was stirred for 15 min. After this time 2-amino-3-bromo-5-phenylpyrazine 17b (0.05 g, 0.2 mmol) was added and the mixture heated at 80° C. for 4 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 petroleum ether-EtOAc (7:3 v/v) as eluent, to obtain 0.04 g of the title compound 18o as a yellow oil (62% yield). 1H-NMR (CDCl3): 1.73 (s, 6H), 2.08 (s, 3H), 2.23 (s, 6H), 5.13 (br s, 2H), 7.32-7.36 (m, 1H), 7.42-7.46 (m, 2H), 7.91-7.93 (m, 2H), 8.29 (s, 1H). MS (ESI): m/z 338 (M+H+).

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