Réaction #1121778

Équation de réaction

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

1-adamantanethiol

sodium hydride

→

title compound 18o

Rendement 62.0%

2-Amino-5-phenyl-3-adamantylthiopyrazine

Rendement 62.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Autrequenched with water
3. 3
   workup.ADDITIONThen EtOAc was added
4. 4
   Filtrationfiltered
5. 5
   Autrethe solvent removed under reduced pressure
6. 6
   Autreto get a crude that
7. 7
   Autrewas purified by flash chromatography

Mode opératoire

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+).

Source