Potassium Persulfate → 4,6-Dichloropyrimidine-5-carboxylic acid

HRID 511559

Reaction equation

HRID 511559 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:12].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:7]([C:8]([OH:12])=[O:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24412Potassium PersulfateHCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

Product 1

HCID 248204874,6-Dichloropyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4,6-dichloro-5-pyrimidinecarbaldehyde (15.0 g, 84.8 mmol) in DMF (360 mL) was charged with potassium monopersulfate (38.9 g, 254 mmol) and stirred over night at rt. The reaction mixture was filtered through a pad of celite and partitioned between EtOAc and water and separated. The aqueous was extracted with EtOAc (3×) and the combined organic fractions were washed with water (2×), brine, and dried over sodium sulfate, filtered, and concentrated to afford the title compound. 1H NMR (DMSO-d6, 400 MHz): δ=9.02 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. custompartitioned between EtOAc and water
  3. customseparated
  4. extractionThe aqueous was extracted with EtOAc (3×)
  5. washthe combined organic fractions were washed with water (2×), brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e5d7e8ae45ca4acb93f935f4486f2a5a
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Linked notes

Loading…