Ethanol → 2-(3-Pyridyl)-6-(4-pyridyl)pyrimidin-4-one

HRID 853786

Reaction equation

HRID 853786 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[CH2:8][C:9]([O:11]CC)=O)=[CH:3][CH:2]=1.Cl.[C:16]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)(=[NH:18])[NH2:17].C(=O)([O-])[O-].[K+].[K+].C(O)C>C(O)(=O)C>[N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:16]2[NH:18][C:9](=[O:11])[CH:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[N:17]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 202042Nicotinamidine hydrochlorideHCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionate

Product 1

HCID 1354093932-(3-Pyridyl)-6-(4-pyridyl)pyrimidin-4-oneYield 50.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

ethyl 3-(4-pyridyl)-3-oxopropionate (0.60 g), 3-amidinopyridine hydrochloride (0.54 g) and potassium carbonate (1.15 g) were added to 5 ml of ethanol, and the mixture was heated under reflux at 75° C. for 20 hours. Acetic acid was added to the reaction mixture, and the solvent was removed by distillation. The residue was added with water and then with acetic acid, and the resulting solid was separated by filtration, washed with water and ethyl acetate, and dried to obtain 0.39 g of the desired compound.

Workup

  1. temperaturethe mixture was heated
  2. customthe solvent was removed by distillation
  3. additionThe residue was added with water
  4. customwith acetic acid, and the resulting solid was separated by filtration
  5. washwashed with water and ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-80f553bfe6ea4338b734b2fe6562c22a
Source dataset
uspto-grants-2007_08
Patent number
US07256199B1

Linked notes

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