Trifluoroacetic acid → (3-methoxy-6-oxopyrido(2,3-b)pyrazin-5(6H)-yl)acetaldehyde

HRID 1510667Notes

Reaction equation

HRID 1510667 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:12]2=[N:13][C:14]([O:17][CH3:18])=[CH:15][N:16]=[C:11]2[CH:10]=[CH:9][C:8]1=[O:19].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:18][O:17][C:14]1[N:13]=[C:12]2[N:7]([CH2:6][CH:2]=[O:1])[C:8](=[O:19])[CH:9]=[CH:10][C:11]2=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 578154155-(1,3-dioxolan-2-ylmethyl)-3-methoxypyrido(2,3-b)pyrazin-6(5H)-one

Product 1

HCID 57815393(3-methoxy-6-oxopyrido(2,3-b)pyrazin-5(6H)-yl)acetaldehydeYield 120.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.12 g of 5-(1,3-dioxolan-2-ylmethyl)-3-methoxypyrido(2,3-b)pyrazin-6(5H)-one, 5 mL of a 90% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 3 hours 30 minutes. A saturated aqueous sodium hydrogen carbonate solution and chloroform were added to the reaction mixture, the organic layer was separated and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.12 g of (3-methoxy-6-oxopyrido(2,3-b)pyrazin-5(6H)-yl)acetaldehyde as a light yellow solid.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with chloroform
  3. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-808a53e9a9a84f8cb81e947b80e615c8
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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