Sodium periodate → [7-(methyloxy)-2-oxopyrido[2,3-b]pyrazin-1(2H)-yl]acetaldehyde

HRID 656998Notes

Reaction equation

HRID 656998 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[N:15][C:6]2[N:7]=[CH:8][C:9](=[O:14])[N:10]([CH2:11][CH:12]=C)[C:5]=2[CH:4]=1.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:16]=[N:15][C:6]2[N:7]=[CH:8][C:9](=[O:14])[N:10]([CH2:11][CH:12]=[O:18])[C:5]=2[CH:4]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 689936507-(Methyloxy)-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 57815437[7-(methyloxy)-2-oxopyrido[2,3-b]pyrazin-1(2H)-yl]acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

7-(Methyloxy)-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one (846 mg, 3.900 mmol) was dissolved in 1,4-dioxane (20 ml) and water (10 ml). Sodium periodate (20.09 g, 9.75 mmol) was added, followed by osmium tetroxide (0.83 ml of 4% aqueous solution). The mixture stirred at rt for 4 h, and then extracted with 20% MeOH/DCM (3×200 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give [7-(methyloxy)-2-oxopyrido[2,3-b]pyrazin-1(2H)-yl]acetaldehyde (existing mostly as the methyl hemiacetal) as an impure brown solid (969 mg, 113%).

Workup

  1. extractionextracted with 20% MeOH/DCM (3×200 ml)
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f93975d259804b7ba2a23a863909419e
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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