Reaction #1121779

Reaction equation

2-amino-3-bromo-5-phenylpyrazine

2-Amino-3-Bromo-5-phenylpyrazine

2-mercaptobenzothiazol

sodium hydride

→

title compound 18p

Yield 23.0%

2-Amino-3-(benzo[d]thiazol-2-ylthio)-5-phenylpyrazine

Yield 23.0%

Solvents

DMF

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   workup.ADDITIONthe crude was diluted with dichloromethane
3. 3
   Washwashed with water
4. 4
   Filtrationfiltered
5. 5
   Otherthe solvent removed under reduced pressure
6. 6
   Otherto get a crude that
7. 7
   Otherwas purified by flash chromatography

Procedure

To a solution of 2-mercaptobenzothiazol (0.07 g, 0.4 mmol) in dry DMF (7 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 110° C. for 4 h. The solvent was removed under reduced pressure and the crude was diluted with dichloromethane, washed with water. Then 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) to get 15 mg of title compound 18p as a pale yellow solid (yield 23%). 1H-NMR (CDCl3): 5.36 (br s, 2H), 7.28-7.47 (m, 6H), 7.59-7.76 (m, 1H), 7.91-7.93 (m, 2H), 8.53 (s, 1H). MS (ESI): m/z 359 (M+Na1).

Source