Potassium Hydroxide → 2,4-dimethylpyrimidine-5-carboxylic acid

HRID 1268745Notes

Reaction equation

HRID 1268745 reaction equation
[OH-].[K+].[CH3:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([C:11]([O:13]CC)=[O:12])=[CH:6][N:5]=1>C(O)C>[CH3:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([C:11]([OH:13])=[O:12])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 295888Ethyl 2,4-dimethylpyrimidine-5-carboxylate

Product 1

HCID 64875952,4-dimethylpyrimidine-5-carboxylic acidYield 59.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of potassium hydroxide (67 g, 1.0 mol) in 95% ethanol (300 mL) was added to a solution of ethyl 2,4-dimethyl-5-pyrimidinecarboxate (73 g, 0.40 mol) in 95% ethanol (100 mL) and the mixture was heated under reflux for 5 hrs. Ethanol was evaporated under reduced pressure, and the residue was dissolved in water, and the aqueous solution was acidified with conc. hydrochloric acid. Precipitated solids were collected by filtration, washed with water and dried to give the title compound (36 g, yield 58%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. customEthanol was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. customPrecipitated solids
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-5482ea86e6e7451f991255e3056c5869
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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