Sodium Hydroxide → 4-Ethylamino-2-methylthiopyrimidine-5-carboxylic acid

HRID 871839Notes

Reaction equation

HRID 871839 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1)[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([NH:3][C:4]1[C:9]([C:10]([OH:12])=[O:11])=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10514260Ethyl 4-(ethylamino)-2-(methylthio)pyrimidine-5-carboxylate

Product 1

HCID 222201684-Ethylamino-2-methylthiopyrimidine-5-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture containing 6.33 g (26.0 mmol) of ethyl 4-ethylamino-2-methylthio-5-pyrimidinecarboxylate, 65 mL (65.0 mmol) of 1N NaOH and 60 mL of ethanol is refluxed for 1 hour. The ethanol is evaporated off under reduced pressure and the residue is diluted in 100 mL of water. 65 mL of aqueous 1N HCl solution are added and the white precipitate formed is drained by suction. The solid is rinsed with water and dried under vacuum. 5.1 g of expected product are obtained in the form of a white solid. Melting point=188°C. Yield=92%.

Workup

  1. temperatureis refluxed for 1 hour
  2. customThe ethanol is evaporated off under reduced pressure
  3. additionthe residue is diluted in 100 mL of water
  4. addition65 mL of aqueous 1N HCl solution are added
  5. customthe white precipitate formed
  6. washThe solid is rinsed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-20558241aeed426fb1b3e1f0eeafe494
Source dataset
uspto-grants-2015_03
Patent number
US08975250B2

Reaction notes

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