Potassium Permanganate → Ethyl 2-chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carboxylate

HRID 59112Notes

Reaction equation

HRID 59112 reaction equation
I([O-])(=O)(=O)=O.[Na+].[Cl:7][C:8]1[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=C)[CH:11]=[C:10]([CH2:19][O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[N:9]=1.[Mn]([O-])(=O)(=O)=[O:27].[K+]>O.O1CCOCC1>[Cl:7][C:8]1[N:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:27])[CH:11]=[C:10]([CH2:19][O:20][CH2:21][C:22]([F:25])([F:24])[F:23])[N:9]=1

Participants

6

Reactant 3

HCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 1178207992-Chloro-4-(1-ethoxyvinyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine

Product 1

HCID 117821214Ethyl 2-chloro-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium metaperiodate (701 mg, 3.28 mmol) was suspended in water (10 mL) and sonicated until a clear solution was obtained. 2-Chloro-4-(1-ethoxyvinyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine (486 mg, 1.64 mmol) in 1,4-dioxane (20 mL) and potassium permanganate (39 mg, 0.25 mmol) were added and the mixture was stirred at rt for 30 min. The mixture was filtered, precipitate was washed by dioxane and DCM. DCM an solid sodium bicarbonate (s) were added to the filtrate. The mixture was extracted with DCM (×2). The organic phase was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica eluting with DC ti give the title compound as a solid, 385 mg (79%).

Workup

  1. customsonicated until a clear solution
  2. customwas obtained
  3. filtrationThe mixture was filtered
  4. washprecipitate was washed by dioxane and DCM
  5. additionDCM an solid sodium bicarbonate (s) were added to the filtrate
  6. extractionThe mixture was extracted with DCM (×2)
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica eluting with DC ti

Sources & evidence

ORD record
ord-7913c465e5b44fc18988ea5504161201
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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