Ethyl Acetate → Tert-butyl 5-formylpyrazine-2-carboxylate

HRID 217982Notes

Reaction equation

HRID 217982 reaction equation
I([O-])(=O)(=O)=O.[Na+].CN(C)/C=[CH:10]/[C:11]1[N:12]=[CH:13][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:15][CH:16]=1.C(=O)(O)[O-:26].[Na+].C(OCC)(=O)C>O1CCCC1.O>[CH:10]([C:11]1[N:12]=[CH:13][C:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:15][CH:16]=1)=[O:26]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 57475684t-butyl 5-((E)-2-dimethylaminovinyl)pyrazine-2-carboxylate

Product 1

HCID 57475686Tert-butyl 5-formylpyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Sodium periodate (1.67 g) was added to a solution of t-butyl 5-((E)-2-dimethylamino-vinyl)pyrazine-2-carboxylate (645 mg) in 50% tetrahydrofuran-water (26 mL), and the mixture was stirred at room temperature for four hours. A saturated sodium bicarbonate solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The insoluble matter was separated by filtration and the filtrate was concentrated. The residue was purified by silica gel column chromatography to obtain the title compound (249 mg).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe insoluble matter was separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-070903f01a0c4821b6b0673c50ae6954
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

Loading…