4-Chlorobenzamidine → 2-(4-Chloro-phenyl)-5-methyl-3H-pyrimidin-4-one

HRID 2170801

Reaction equation

HRID 2170801 reaction equation
[Na].[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[CH:5][CH:4]=1.C([O:14][C:15](=O)[CH:16]([CH3:19])[CH:17]=O)C>C(O)C>[Cl:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[NH:9][C:15](=[O:14])[C:16]([CH3:19])=[CH:17][N:8]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 2034374-ChlorobenzamidineHCID 5360545SodiumHCID 10898741Ethyl 2-Formylpropionate

Product 1

HCID 599066112-(4-Chloro-phenyl)-5-methyl-3H-pyrimidin-4-oneYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (276 mg, 12 mmol) was added portion wise to ethanol (15 ml) under a nitrogen atmosphere and the mixture allowed to stir at room temperature for 30 minutes until the reaction became homogeneous. 4-Chloro-benzamidine (hydroiodide salt) (1.41 g, 5 mmol) was then added in one portion and the reaction stirred at room temperature for a further 60 minutes. 2-Methyl-3-oxo-propionic acid ethyl ester (716 mg, 5.5 mmol) was finally added drop wise. The reaction was left to stir at room temperature overnight before quenching the reaction slowly with 2M Hydrochloric acid until reaction pH measured pH 1. The resulting precipitate was filtered and air dried, to give 2-(4-Chloro-phenyl)-5-methyl-3H-pyrimidin-4-one as a white solid (570 mg, 2.58 mmol, 52% yield).

Workup

  1. stirringthe reaction stirred at room temperature for a further 60 minutes
  2. waitThe reaction was left
  3. stirringto stir at room temperature overnight
  4. custombefore quenching
  5. customthe reaction slowly with 2M Hydrochloric acid
  6. customuntil reaction pH measured pH 1
  7. filtrationThe resulting precipitate was filtered
  8. customair dried

Sources & evidence

ORD record
ord-03928676cd9942beab34293893f99084
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Linked notes

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