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

HRID 656948Notes

Reaction equation

HRID 656948 reaction equation
[F: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>[F: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 689911287-Fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 86635326(7-fluoro-2-oxopyrido[2,3-b]pyrazin-1(2H)-yl)acetaldehyde

Reagents, catalysts & solvents 3

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

Procedure

7-Fluoro-1-(2-propen-1-yl)pyrido[2,3-b]pyrazin-2(1H)-one (163 mg, 0.795 mmol) was dissolved in 1,4-dioxane (5 ml) and water (5 ml). Sodium periodate (426 mg, 1.99 mmol) was added, followed by osmium tetroxide (0.17 ml of 4% aqueous solution). The mixture stirred at rt for 2 h, and then treated with water (20 ml) and extracted with 20% MeOH/DCM (3×100 ml). The organic extracts were combined, dried over anhydrous magnesium sulphate, filtered and evaporated to give (7-fluoro-2-oxopyrido[2,3-b]pyrazin-1(2H)-yl)acetaldehyde (existing mostly as the methyl hemiacetal) as an impure brown oil (193 mg, 117%).

Workup

  1. extractionextracted with 20% MeOH/DCM (3×100 ml)
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-9407c77755714e5c8bdcf5e729d74e38
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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