Potassium Permanganate → HCID 117821332, compound

HRID 59062Notes

Reaction equation

HRID 59062 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[N:13]=[C:12]([Cl:14])[C:11]([CH3:15])=[C:10]([C:16]([O:18][CH2:19][CH3:20])=C)[N:9]=1.[Mn]([O-])(=O)(=O)=[O:22].[K+]>O.O1CCOCC1>[Cl:7][C:8]1[N:9]=[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:22])[C:11]([CH3:15])=[C:12]([Cl:14])[N:13]=1

Participants

6

Reactant 3

HCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 117821294HCID 117821294, compound

Product 1

HCID 117821332HCID 117821332, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium metaperiodate (2.111 g, 9.87 mmol) was suspended in water (20 mL) and sonicated until a clear solution was obtained. 2,4-Dichloro-6-(1-ethoxyvinyl)-5-methylpyrimidine (1.15 g, 4.93 mmol) dissolved in 1,4-dioxane (40 mL) was added followed by potassium permanganate (0.117 g, 0.74 mmol). The mixture was stirred at rt for 2 h. The mixture was filtered. The filtrate was diluted with saturated solutions of sodium bicarbonate and sodium chloride and extracted twice with ethyl acetate. The organic phase was dried over sodium sulfate, filtered through a pad of silica gel and concentrated in vacuum. Column chromatography on silica gel using a 0-30% gradient of ethyl acetate in heptane yielded the title product, 0.67 g (58%).

Workup

  1. customsonicated until a clear solution
  2. customwas obtained
  3. additionwas added
  4. filtrationThe mixture was filtered
  5. additionThe filtrate was diluted with saturated solutions of sodium bicarbonate and sodium chloride
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered through a pad of silica gel
  9. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-1999ec23252340e788f237d01e299e4f
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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