Ethyl 2-acetyl-3-(dimethylamino)acrylate → HCID 68555848, compound

HRID 2381898Notes

Reaction equation

HRID 2381898 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([NH2:10])=[NH:9].[CH2:11]([O:13][C:14](=[O:23])[C:15](=[CH:19]N(C)C)[C:16](=O)[CH3:17])[CH3:12]>CCO>[CH2:11]([O:13][C:14]([C:15]1[C:16]([CH3:17])=[N:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)=[N:10][CH:19]=1)=[O:23])[CH3:12]

Participants

4

Reactant 2

HCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylateHCID 12403615Pyridine-2-carboximidamide hydrochloride

Product 1

HCID 68555848HCID 68555848, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Na0 (31.7 mmol) is added to anhydrous EtOH (100 mL) and stirred at rt for 15 min. Pyridine-2-carboxamidine hydrochloride (31.7 mmol) is added and the solution is stirred for 15 min. 2-Dimethylaminomethylene-3-oxo-butyric acid ethyl ester (31.7 mmol) is added and the reaction mixture is heated at reflux under N2 for 1 h. The reaction is cooled to rt and concentrated in vacuo. The residue is dissolved in EtOAc (200 mL), washed with brine (2×100 mL), dried (Na2SO4), filtered, and concentrated to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid ethyl ester (6.77 g, 88%). MS: 261 (M+H); 1H 1H NMR (300 MHz, CDCl3): δ 1.44 (t, 3H), 2.97 (s, 3H), 4.44 (q, 2H), 7.44 (m, 1H), 7.91 (m, 1H), 8.60 (m, 1H), 8.90 (m, 1H), 9.31 (s, 1H).

Workup

  1. stirringthe solution is stirred for 15 min
  2. temperaturethe reaction mixture is heated
  3. temperatureat reflux under N2 for 1 h
  4. temperatureThe reaction is cooled to rt
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in EtOAc (200 mL)
  7. washwashed with brine (2×100 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-83002ab280c6419f80f9fef71092b1bc
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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