Citric Acid → HCID 70981544, compound

HRID 2280748Notes

Reaction equation

HRID 2280748 reaction equation
[C:1]([NH:5][C:6]1[C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][N:9]=[C:8]([S:17][CH3:18])[N:7]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)C>[C:1]([NH:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][N:9]=[C:8]([S:17][CH3:18])[N:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 295702HCID 295702, compound

Product 1

HCID 70981544HCID 70981544, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round-bottomed flask ethyl 4-(tert-butylamino)-2-(methylthio)pyrimidine-5-carboxylate (3.2 g, 11.88 mmol) was dissolved in ethanol (40 mL) followed by the addition of 1M aqueous sodium hydroxide solution (35.6 mL, 35.6 mmol). The resulting mixture was stirred overnight at room temperature and then the solvent was evaporated under reduced pressure. After that 2M aqueous citric acid solution (35.6 mL, 71.3 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 a vacuum oven at 45° C. overnight to afford 4-(tert-butylamino)-2-(methylthio)pyrimidine-5-carboxylic acid (2.83 g, 11.73 mmol, 99% yield). MS (ESI) m/z 242.3 [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 a vacuum oven at 45° C. overnight

Sources & evidence

ORD record
ord-106517181ed24892bb4416d67500277b
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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