Ethyl 2-acetyl-3-(dimethylamino)acrylate → Ethyl-2-(4-fluorophenyl)-4-methylpyrimidine-5-carboxylate

HRID 219655Notes

Reaction equation

HRID 219655 reaction equation
Cl.[F:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.[Na].[CH2:13]([O:15][C:16](=[O:25])[C:17]([C:22](=O)[CH3:23])=[CH:18]N(C)C)[CH3:14]>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[C:22]([CH3:23])=[N:8][C:7]([C:6]2[CH:10]=[CH:11][C:3]([F:2])=[CH:4][CH:5]=2)=[N:9][CH:18]=1)=[O:25])[CH3:14]

Participants

5

Reactant 3

HCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateHCID 5360545SodiumHCID 124561604-Fluorobenzamidine Hydrochloride

Product 1

HCID 69279303Ethyl-2-(4-fluorophenyl)-4-methylpyrimidine-5-carboxylateYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Fluorobenzamidine hydrochloride (1.25 g, 7.16 mmol) is added to a solution of sodium metal (0.17 g, 7.39 mmol) in dry ethanol (25 mL) and stirred at room temperature for 20 min. Ethyl-2-acetyl-3-(dimethylamino)acrylate (1.35 g, 7.16 mmol) is added. The mixture is heated to reflux for 3 hours. The solvent is removed in vacuo. The residue is dissolved in EtOAc, washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo to afford ethyl-2-(4-fluorophenyl)-4-methyl-pyrimidine-5-carboxylate (1.65 g, 87%) as a solid. MS: 261 (M+H) 261.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent is removed in vacuo
  4. dissolutionThe residue is dissolved in EtOAc
  5. washwashed with water and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49464ad095e64e3e876387f003083b10
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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