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

HRID 1034597Notes

Reaction equation

[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].[NH2:13][C:14]1[C:19](Br)=[N:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][N:15]=1>CN(C=O)C>[NH2:13][C:14]1[C:19]([S:1][C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[N:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][N:15]=1

Participants

Conditions

Temperature: 110 °C

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).

Workup

customThe solvent was removed under reduced pressure
additionthe crude was diluted with dichloromethane
washwashed with water
filtrationfiltered
customthe solvent removed under reduced pressure
customto get a crude that
customwas purified by flash chromatography

Sources & evidence

ORD record: ord-31db897161a942059148c9ba47e5768b
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546147B2

Reaction notes

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