Sodium Carbonate → 4-Pyrimidinecarboxylic acid

HRID 732018Notes

Reaction equation

HRID 732018 reaction equation
C[N:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH2:3]1.[Mn]([O-])(=O)(=O)=O.[K+].[C:14](=O)([O-:16])[O-:15].[Na+].[Na+]>O>[N:2]1[CH:7]=[CH:6][C:5]([C:14]([OH:16])=[O:15])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 516875Potassium PermanganateHCID 189740881-Methylpyrimidine

Product 1

HCID 1693064-Pyrimidinecarboxylic acidYield 11%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Methyl-pyrimidine (9.41 g, 100 mmol), potassium permanganate (26.9 g) and sodium carbonate (10.6 g) was refluxed in water (100 ml) for 72 h followed by filtration through celite. The filtrate was washed with several portions of DCM and EtOAc before acidification with conc. HCl. The formed precipitate was collected and washed with water to yield 1.37 g of the title compound as a white solid. 1H NMR (DMSO-d6) d (ppm): 13.94 (br. s, 1H), 9.37 (d, 1H), 9.07 (d, 1H), 8.01 (dd, 1H).

Workup

  1. filtrationfollowed by filtration through celite
  2. washThe filtrate was washed with several portions of DCM and EtOAc before acidification with conc. HCl
  3. customThe formed precipitate was collected
  4. washwashed with water

Sources & evidence

ORD record
ord-c5349d8e57b94fcca56363d44267a61c
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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