Trifluoroacetic acid → (6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde

HRID 385500Notes

Reaction equation

HRID 385500 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[N:10][C:9]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[N:17][C:8]1=2.FC(F)(F)C(O)=O>>[CH3:19][O:18][C:16]1[CH:15]=[CH:14][C:9]2[N:10]=[CH:11][C:12](=[O:13])[N:7]([CH2:6][CH:2]=[O:1])[C:8]=2[N:17]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 578152174-((1,3-Dioxolan-2-yl)methyl)-6-methoxypyrido[3,2-b]pyrazin-3(4h)-one

Product 1

HCID 57815220(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehydeYield 102.9%

Procedure

To 0.21 g of 4-(1,3-dioxolan-2-ylmethyl)-6-methoxypyrido(2,3-b)pyrazin-3(4H)-one, 10 mL of an 80% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 5 hours and then left overnight. The solvent was distilled off under reduced pressure. The resultant residue was charged with ethyl acetate and water and adjusted to pH 7.0 with a 1 mol/L aqueous sodium hydroxide solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.18 g of (6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde as a light brown foam.

Workup

  1. waitleft overnight
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionThe resultant residue was charged with ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2d7109632fce489ba19e2b22fbcae164
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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