Sodium hydride → 3-(5-(methylthio)-1,3,4-thiadiazol-2-ylthio)pyrazine-2-carbonitrile

HRID 1968389Notes

Reaction equation

[CH3:1][S:2][C:3]1[S:7][C:6]([SH:8])=[N:5][N:4]=1.[H-].[Na+].Cl[C:12]1[C:13]([C:18]#[N:19])=[N:14][CH:15]=[CH:16][N:17]=1>CN(C=O)C.C1C=CC=CC=1>[CH3:1][S:2][C:3]1[S:7][C:6]([S:8][C:12]2[C:13]([C:18]#[N:19])=[N:14][CH:15]=[CH:16][N:17]=2)=[N:5][N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-(methylthio)-1,3,4-thiadiazole-2-thiol (821 mg, 5.0 mmol) in DMF and benzene (10 ml, 1/1) was added NaH (60% dispersion in mineral oil, 220 mg, 5.5 mmol) slowly at 0° C. under nitrogen atmosphere. The resulting suspension was stirred at 0° C. for 15 minutes and then to the mixture was added 3-chloropyrazine-2-carbonitrile (698 mg, 5.0 mmol). The reaction was stirred at 80° C. for 4 hr. The reaction was then cooled to room temperature and quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with water, brine and dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel to give the title compound as a white solid.

Workup

stirringThe reaction was stirred at 80° C. for 4 hr
temperatureThe reaction was then cooled to room temperature
customquenched with saturated NH4Cl solution
extractionextracted with EtOAc
washThe combined organic layers were washed with water, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-92e6f8105c1f43dbab2d3d74c05faeca
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426358B2

Reaction notes

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