Acetamidine monohydrochloride → Ethyl 2,4-dimethylpyrimidine-5-carboxylate

HRID 1408520Notes

Reaction equation

HRID 1408520 reaction equation
CN([CH:4]=[C:5]([C:11](=O)[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.Cl.[C:15]([NH2:18])(=[NH:17])[CH3:16].CC[O-].[Na+]>CCO>[CH3:16][C:15]1[N:18]=[C:11]([CH3:12])[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:17]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 2723922Sodium ethoxideHCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylate

Product 1

HCID 295888Ethyl 2,4-dimethylpyrimidine-5-carboxylateYield 42.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate 51 (17.6 g, 95 mmol) and acetamidine hydrochloride (17.6 g, 95 mmol), were dissolved in EtOH and added NaOEt (6.5 g, 95 mmol). This mixture was refluxed for 4 h. After that, ethanol removed on rotavapour followed by work-up (AcOEt/H2O) to obtain the crude. Crude was purified by column chromatography using 60-120 mesh silicagel and AcOEt and Petether (25:75) as eluent to obtain the title compound (7.3 g).

Workup

  1. temperatureThis mixture was refluxed for 4 h
  2. customAfter that, ethanol removed on rotavapour
  3. customto obtain the crude
  4. customCrude was purified by column chromatography

Sources & evidence

ORD record
ord-a434670dd69b4fbba7546237ab92a269
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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