Formamidine acetate → Ethyl 4-methylpyrimidine-5-carboxylate

HRID 1408518Notes

Reaction equation

HRID 1408518 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]([C:11](=O)[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C(O)(=O)C.C(N)=[NH:19].CC[O-].[Na+]>CCO>[CH3:12][C:11]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:2]=[CH:1][N:19]=1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 2723922Sodium ethoxideHCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylate

Product 1

HCID 13192893Ethyl 4-methylpyrimidine-5-carboxylateYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Intermediate 51 (9.7 g, 52.4 mmol) and Formamidine acetate (5.4 g, 52.4 mmol), were dissolved in EtOH and added NaOEt (3.6 g, 52.4 mmol). This mixture was refluxed for 6 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 (2.7 g).

Workup

  1. temperatureThis mixture was refluxed for 6 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-a95e6d22b59345d09ac850005288ed62
Source dataset
uspto-grants-2014_12
Patent number
US08921364B2

Reaction notes

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