Reacción #1121778

Ecuación de reacción

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

1-adamantanethiol

sodium hydride

→

title compound 18o

Rendimiento 62.0%

2-Amino-5-phenyl-3-adamantylthiopyrazine

Rendimiento 62.0%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   Otroquenched with water
3. 3
   workup.ADDITIONThen EtOAc was added
4. 4
   Filtraciónfiltered
5. 5
   Otrothe solvent removed under reduced pressure
6. 6
   Otroto get a crude that
7. 7
   Otrowas purified by flash chromatography

Procedimiento

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+).

Fuente