Acetonitrile → HCID 86690965, compound

HRID 1055675Notes

Reaction equation

HRID 1055675 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].[C:11](#[N:13])[CH3:12].[H-].[Na+:15].C(OC)(C)(C)C>C1COCC1>[C:11]([CH:12]=[C:3]([C:5]1[CH:10]=[N:9][CH:8]=[CH:7][N:6]=1)[O-:4])#[N:13].[Na+:15]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 72662Methyl pyrazinoate

Product 1

HCID 86690965HCID 86690965, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.5 g (10.9 mmol) of methylpyrazine-2-carboxylate and 446 mg (10.9 mmol) of acetonitrile in 16.5 ml of THF was added dropwise to a suspension, heated under reflux, of 434 mg of sodium hydride (60% strength suspension in mineral oil) in 10 ml of THF. The reaction mixture was heated under reflux for 20 h. After cooling, 50 ml of methyl tert-butyl ether were added and the mixture was stirred for 30 minutes. The precipitate formed was filtered off with suction over a frit and dried under oil pump vacuum. This gave 1.77 g (96% of theory) of the title compound which was used without further characterization for the next step.

Workup

  1. temperatureheated
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 20 h
  4. temperatureAfter cooling
  5. customThe precipitate formed
  6. filtrationwas filtered off with suction over a frit
  7. customdried under oil pump vacuum

Sources & evidence

ORD record
ord-0231efb821f049cb991d235e4465c37d
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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