تفاعل #1121775

معادلة التفاعل

2-amino-3-bromo-5-(4-methoxyphenyl)pyrazine

2-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

thiophenol

sodium hydride

→

title compound 18a

المردود 70.0%

2-Amino-5-(4-methoxyphenyl)-3-phenylthiopyrazine

المردود 70.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture refluxed for 6 h
2. 2
   درجة الحرارةcooled
3. 3
   استخلاصextracted with EtOAc
4. 4
   غسيلThe organic layer was washed with water
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   أخرىthe solvent removed under reduced pressure
8. 8
   أخرىto get a crude that
9. 9
   أخرىwas purified by flash chromatography

الإجراء التجريبي

To a cooled solution of thiophenol (0.08 mL, 0.7 mmol) in dry DMF (10 mL), sodium hydride (NaH) (0.025 g, 1.00 mmol) was added and the resulting mixture was stirred for 15 min at 5-10° C. After this time 2-amino-3-bromo-5-(4-methoxyphenyl)pyrazine 17a (0.20 g, 0.71 mmol) was added and the mixture refluxed for 6 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 (65:45 v/v) as eluent, to obtain 0.15 g of the title compound 18a as an orange solid (mp 89-90° C., 70% yield). 1H-NMR (CDCl3): 3.81 (s, 3H), 4.90 (br s, 2H), 6.89 (d, J=8.7, 2H), 7.33-7.39 (m, 7.45-7.50 (m, 2H), 7.69 (d, J=8.7, 2H), 8.28 (s, 1H). MS (ESI): m/z 310 (M+H+).

المصدر