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

HRID 656998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656998
[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

Komponenten

6

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 30318Osmium TetroxideKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f93975d259804b7ba2a23a863909419e
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

Notizen zur Reaktion

Wird geladen…