Sodium Hydroxide → 2-Methoxy-6-methylpyrimidine-4-carboxylic acid

HRID 1109978Notes

Reaction equation

HRID 1109978 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([O:11]C)=[O:10])[CH:6]=[C:5]([CH3:13])[N:4]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=[O:10])[CH:6]=[C:5]([CH3:13])[N:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19018471Methyl 2-methoxy-6-methylpyrimidine-4-carboxylate

Product 1

HCID 190184722-Methoxy-6-methylpyrimidine-4-carboxylic acidYield 46.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

15.5 g of methyl 2-methoxy-6-methylpyrimidine-4-carboxylate are added to a stirred solution of 3.6 g of sodium hydroxide in 100 ml of methanol and 10 ml of water. Stirring is continued at room temperature until the starting material disappears (TLC checking; 3 h). The methanol is distilled off under reduced pressure, the residue is taken up in water and the mixture is extracted once with ethyl acetate. The aqueous phase is acidified to pH 2 with conc. hydrochloric acid and then stirred for 1 h, and the product is filtered off with suction. 6.6 g of 2-methoxy-6-methylpyrimidine-4-carboxylic acid of melting point 161°-163° C. are obtained in this way. Concentration and extraction of the mother liquor using dichloromethane additionally gives 3.1 g of product of melting point 159°-161° C.

Workup

  1. customis continued at room temperature until the starting material
  2. custom(TLC checking; 3 h)
  3. distillationThe methanol is distilled off under reduced pressure
  4. extractionthe mixture is extracted once with ethyl acetate
  5. stirringstirred for 1 h
  6. filtrationthe product is filtered off with suction

Sources & evidence

ORD record
ord-4bb449d3169a43248c0fc265a6e2b90d
Source dataset
uspto-grants-1994_06
Patent number
US05324710

Reaction notes

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