Tetrahydrofuran → 2-Cyano-6-[2-(dimethylamino)ethylthio]pyrazine

HRID 748385Notes

Reaction equation

HRID 748385 reaction equation
Cl.[CH3:2][N:3]([CH3:7])[CH2:4][CH2:5][SH:6].[H-].[Na+].C1COCC1.Cl[C:16]1[CH:21]=[N:20][CH:19]=[C:18]([C:22]#[N:23])[N:17]=1>O.C(OCC)(=O)C>[C:22]([C:18]1[CH:19]=[N:20][CH:21]=[C:16]([S:6][CH2:5][CH2:4][N:3]([CH3:7])[CH3:2])[N:17]=1)#[N:23]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 25798Captamine HydrochlorideHCID 813036-Chloropyrazine-2-carbonitrile

Product 1

HCID 229395352-Cyano-6-[2-(dimethylamino)ethylthio]pyrazineYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Dimethylaminoethanethiol hydrochloride salt (1.46 g, 10.0 mmol) and sodium hydride (60% in oil, 0.88 g, 22.0 mmol) were added to THF (50 ml), and 2-chloro-6-cyanopyrazine (1.40 g, 10.0 mmol) was added thereto. The mixture was stirred at room temperature for 18 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from n-hexane-ethyl acetate to give the titled compound (1.00 g, 48%) as pale yellow crystals.

Workup

  1. additionwas added
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-bc6b404debb246f398d12e8379bd1512
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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