反応 #1121777

反応方程式

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

cyclopentanethiol

sodium hydride

→

title compound 18n

収率 67.6%

2-Amino-5-phenyl-3-cyclopentylthiopyrazine

収率 67.6%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度cooled
2. 2
   その他quenched with water
3. 3
   workup.ADDITIONThen EtOAc was added
4. 4
   ろ過filtered
5. 5
   その他the solvent removed under reduced pressure
6. 6
   その他to get a crude that
7. 7
   その他was purified by flash chromatography

実験手順

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).

出典