Citric Acid → 4-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic Acid

HRID 2280744Notes

Reaction equation

HRID 2280744 reaction equation
[CH:1]([NH:4][C:5]1[C:10]([C:11]([O:13]CC)=[O:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[CH:1]([NH:4][C:5]1[C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=[C:7]([S:16][CH3:17])[N:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 10491237HCID 10491237, compound

Product 1

HCID 127840854-(Isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic AcidYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round-bottomed flask ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate (10.97 g, 43.0 mmol) was dissolved in ethanol (150 mL) followed by the addition of aqueous sodium hydroxide solution (1M, 129 ml, 129 mmol). The resulting mixture was stirred overnight at room temperature and then the solvent was evaporated under reduced pressure. Aqueous citric acid solution (2M, 129 ml, 258 mmol) was slowly added and the resulting mixture was stirred for 0.5 h at room temperature. The suspension was filtered and the solids were washed twice with water (2×50 mL) and then dried in the vacuum oven at 45° C. overnight to afford 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylic acid (8.38 g, 36.9 mmol, 86% yield); MS (ESI) m/z 228.4 [M+1]+.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. stirringthe resulting mixture was stirred for 0.5 h at room temperature
  3. filtrationThe suspension was filtered
  4. washthe solids were washed twice with water (2×50 mL)
  5. customdried in the vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-cbe891caf7d844d2997daba2c6c2421f
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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