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

HRID 657104Notes

Reaction equation

HRID 657104 reaction equation
FC(F)(F)C(O)=O.C[O:9][CH:10](OC)[CH2:11][N:12]1[C:17](=[O:18])[CH:16]=[N:15][C:14]2[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[N:22][C:13]1=2>O>[CH3:24][O:23][C:21]1[CH:20]=[CH:19][C:14]2[N:15]=[CH:16][C:17](=[O:18])[N:12]([CH2:11][CH:10]=[O:9])[C:13]=2[N:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 533021904-(2,2-Dimethoxyethyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroacetic acid (3 mL) was added to 4-[2,2-bis(methyloxy)ethyl]-6-(methyloxy)pyrido[2,3-b]pyrazin-3(4H)-one (0.9 g, 3.4 mmol) in water (3 mL) at room temperature and stirred for 2 h. The reaction mixture was concentrated and the residue was purified by column chromatography (silica gel) using a 0-10% MeOH/DCM/1% NH4OH gradient to give the product as a mixture of aldehyde and hemiacetal (0.6 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by column chromatography (silica gel)
  3. customto give the product

Sources & evidence

ORD record
ord-f1ed18b7e881447497e4fb9435482c2a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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