Selenium Dioxide → Pyrido[2,3-b]pyrazine-6-carbaldehyde

HRID 642867Notes

Reaction equation

HRID 642867 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([N:11]=1)=[N:7][CH:8]=[CH:9][N:10]=2.[Se](=O)=[O:13]>O1CCOCC1>[N:10]1[CH:9]=[CH:8][N:7]=[C:6]2[N:11]=[C:2]([CH:1]=[O:13])[CH:3]=[CH:4][C:5]=12

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 104193166-Methylpyrido[2,3-b]pyrazine

Product 1

HCID 11542824Pyrido[2,3-b]pyrazine-6-carbaldehydeYield 50.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

6-Methyl-pyrido[2,3-b]pyrazine (100 mg, 0.69 mmol) was dissolved in dioxane. Selenium dioxide (269 mg, 2.4 mmol) was added, and the suspension was refluxed at 110° C. for 3 minutes. The reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate was washed with brine, dried using magnesium sulfate, and concentrated to yield the title product (55 mg, 50%) as a pink solid. 1H NMR (DMSO-d6): δ=8 s, 1H), 9.31 (d, 1H,J=1.6 Hz), 9.21 (d, 1H, J=1.6 Hz), 8.81 (d, 1H, J=8.5 Hz), 8.42 (d, 1H, J=8.5 Hz). Calculated mass=159, [M+H]+=160.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe ethyl acetate was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-46ac8c4060584b12ac18cba847d4c670
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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