تفاعل #1121777

معادلة التفاعل

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

cyclopentanethiol

sodium hydride

→

title compound 18n

المردود 67.6%

2-Amino-5-phenyl-3-cyclopentylthiopyrazine

المردود 67.6%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled
2. 2
   أخرىquenched with water
3. 3
   workup.ADDITIONThen EtOAc was added
4. 4
   ترشيحfiltered
5. 5
   أخرىthe solvent removed under reduced pressure
6. 6
   أخرىto get a crude that
7. 7
   أخرىwas purified by flash chromatography

الإجراء التجريبي

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).

المصدر