Hydrogen Peroxide → 5-(4-[1,3]Dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carboxamide

HRID 492446Notes

Reaction equation

HRID 492446 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[N:12]=[CH:13][C:14]([C:17]#[N:18])=[N:15][CH:16]=2)=[C:8]([CH3:21])[CH:7]=1.C([O-])([O-])=[O:23].[K+].[K+].OO>CS(C)=O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:20]=[CH:19][C:9]([O:10][C:11]2[N:12]=[CH:13][C:14]([C:17]([NH2:18])=[O:23])=[N:15][CH:16]=2)=[C:8]([CH3:21])[CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 597300525-(4-[1,3]Dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carbonitrile

Product 1

HCID 597302765-(4-[1,3]Dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carboxamideYield 137.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Take up 5-(4-[1,3]dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carbonitrile (0.082 g, 0.305 mmol) and K2CO3 (0.020 g, 0.152 mmol) in DMSO (3.0 mL). Add 30% H2O2 (0.090 mL, 0.792 mmol) and stir at room temperature for 1.5 hours before quenching with water (10 mL). Extract with ethyl acetate (50 mL). Wash the organic layer with water (1× 10 mL), dry over Na2SO4, filter and concentrate. Purify by flash chromatography, eluting with 40% ethyl acetate in dichloromethane to give the title compound (0.063 g, 68.6%): MS ES+ 302.0 (M+H)+; TLC [silica gel 60 F254, 40% ethyl acetate in dichloromethane] Rf=0.17.

Workup

  1. custombefore quenching with water (10 mL)
  2. extractionExtract with ethyl acetate (50 mL)
  3. washWash the organic layer with water (1× 10 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by flash chromatography
  8. washeluting with 40% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-832d6a4c43fc4560886460dda4eb5781
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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