Acetone → 5-Ethylpyrimidine-4-carboxylic acid

HRID 1527643Notes

Reaction equation

HRID 1527643 reaction equation
[CH2:1]([C:3]1[C:4]([C:9]2[O:10]C=CC=2)=[N:5][CH:6]=[N:7][CH:8]=1)[CH3:2].CC(C)=[O:16].[Mn]([O-])(=O)(=O)=O.[K+].C(=O)([O-])O.[Na+]>O>[CH2:1]([C:3]1[C:4]([C:9]([OH:10])=[O:16])=[N:5][CH:6]=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 678106955-Ethyl-4-(furan-2-yl)-pyrimidine

Product 1

HCID 678120845-Ethylpyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-ethyl-4-(furan-2-yl)-pyrimidine (2.03 g), acetone (70 ml), and water (35 ml) was stirred at 50° C., potassium permanganate (15 g) was added thereto over 15 minutes, and the reaction mixture was stirred under reflux for 1 hour. After standing to cool the reaction mixture to room temperature, to the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with tert-butyl methyl ether. To the resulting aqueous layer, hydrochloric acid was added, and extracted with tert-butyl methyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 1.14 g of 5-ethyl-pyrimidine-4-carboxylic acid.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureunder reflux for 1 hour
  3. temperatureto cool the reaction mixture to room temperature
  4. extractionextracted with tert-butyl methyl ether
  5. additionTo the resulting aqueous layer, hydrochloric acid was added
  6. extractionextracted with tert-butyl methyl ether
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-753da51736544f89aa051f4cf5c42177
Source dataset
uspto-grants-2015_07
Patent number
US09089136B2

Reaction notes

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