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

HRID 656933Notes

Reaction equation

HRID 656933 reaction equation
[Br:1][C:2]1[CH:15]=[N:14][C:5]2[N:6]=[CH:7][C:8](=[O:13])[N:9]([CH2:10][CH:11]=C)[C:4]=2[CH:3]=1.I([O-])(=O)(=O)=[O:17].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:15]=[N:14][C:5]2[N:6]=[CH:7][C:8](=[O:13])[N:9]([CH2:10][CH:11]=[O:17])[C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 688205297-bromo-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 86635321(7-bromo-2-oxopyrido[2,3-b]pyrazin-1(2H)-yl)acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

7-Bromo-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one (278 mg, 1.045 mmol) was dissolved in 1,4-dioxane (10 ml) and water (10 ml). Sodium periodate (559 mg, 2.613 mmol) was added, followed by osmium tetroxide (0.22 ml of 4% aqueous solution). The mixture stirred at rt for 1 h, water 40 ml was added the mixture was stirred for a further 1 h. The reaction was concentrated to about 50 ml and extracted with 20% MeOH/DCM (3×100 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give (7-bromo-2-oxopyrido[2,3-b]pyrazin-1(2H)-yl)acetaldehyde (existing mostly as the hydrate) as an impure brown oil (423 mg, 107%).

Workup

  1. stirringwas stirred for a further 1 h
  2. concentrationThe reaction was concentrated to about 50 ml
  3. extractionextracted with 20% MeOH/DCM (3×100 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a2c1331c00b74acabe4d7887166c29d1
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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