تفاعل #1121780

معادلة التفاعل

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

phenol

sodium hydride

→

title compound 18q

المردود 62.0%

2-Amino-5-phenyl-3-phenoxypyrazine

المردود 62.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture refluxed for 20 h
2. 2
   درجة الحرارةcooled
3. 3
   استخلاصextracted with EtOAc
4. 4
   غسيلThe organic layer was washed with water
5. 5
   ترشيحfiltered
6. 6
   أخرىthe solvent removed under reduced pressure
7. 7
   أخرىto get a crude that
8. 8
   أخرىwas purified by flash chromatography

الإجراء التجريبي

To a cooled solution of phenol (0.07 mL, 0.80 mmol) in dry DMF (5 mL), sodium hydride (NaH) (0.02 g, 0.80 mmol) was added and the resulting mixture was cooled at 5-10° C. and stirred for 15 min. After this time 2-amino-3-bromo-5-phenylpyrazine 17b (0.25 g, 1.00 mmol) was added and the mixture refluxed for 20 h, cooled and extracted with EtOAc. The organic layer was washed with water, anidrified over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using dichloromethane-EtOAc (70:30 v/v) as eluent, to obtain 0.13 g of the title compound 18q as a pink solid (mp 129-131° C., 62% yield). 1H-NMR (CDCh): 5.04 (br s, 2H), 7.28-7.43 (m, 8H), 7.69-7.73 (m, 2H), 8.18 (s, 1H). MS (ESI): m/z 264 (M+H+).

المصدر