Sodium ethoxide → Ethyl-2-(4-pyridyl)-5-pyrimidinecarboxylic Acid

HRID 352774

Reaction equation

HRID 352774 reaction equation
[O-][CH2:2][CH3:3].[Na+].Cl.[C:6]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)(=[NH:8])[NH2:7].[CH:15]([CH:17]([CH:23]=O)[C:18]([O:20]CC)=[O:19])=O>C(O)C>[CH2:2]([C:15]1[C:17]([C:18]([OH:20])=[O:19])=[CH:23][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:8]=1)[CH3:3]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 2776844Pyridine-4-amidine hydrochlorideHCID 11029955Ethyl 2-formyl-3-oxopropanoate

Product 1

HCID 22710304Ethyl-2-(4-pyridyl)-5-pyrimidinecarboxylic AcidYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium ethoxide (590 mg) was dissolved in anhydrous ethanol (50 ml) at room temperature. To the resulting solution, 4-amidinopyridine hydrochloride (1.31 g) was added, followed by the dropwise addition of a solution of ethyl 2,2-diformylacetate (1.20 g) in anhydrous ethanol (50 ml). The resulting mixture was heated under reflux for 6 hours. To the residue obtained by distilling off the solvent under reduced pressure, dichloromethane and water were added. The organic layer thus separated was dried over anhydrous sodium sulfate. After the solvent was concentrated under reduced pressure, the residue was crystallized in ethanol, whereby the title compound (279 mg, 15%) was obtained as colorless crystals.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. customTo the residue obtained
  4. distillationby distilling off the solvent under reduced pressure, dichloromethane and water
  5. additionwere added
  6. customThe organic layer thus separated
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. concentrationAfter the solvent was concentrated under reduced pressure
  9. customthe residue was crystallized in ethanol

Sources & evidence

ORD record
ord-967aba538dbf4028b42d4705cf39787f
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Linked notes

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