Pyridine → 4-(3-Chlorophenyl)-3-ethoxycarbonyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

HRID 24616Notes

Reaction equation

HRID 24616 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:7][C:8]1[CH:9]=[C:10]([CH:14]2[C:19]([C:20]([O:22]CC3C=CC=CC=3)=O)=[C:18]([CH3:30])[NH:17][C:16]([O:31]C)=[N:15]2)[CH:11]=[CH:12][CH:13]=1.Cl[C:34]([O:36][CH2:37][CH3:38])=[O:35]>C(OCC)(=O)C>[C:3]1([CH:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:5][CH2:6][NH:1][C:20]([C:19]2[CH:14]([C:10]3[CH:11]=[CH:12][CH:13]=[C:8]([Cl:7])[CH:9]=3)[N:15]([C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:16](=[O:31])[NH:17][C:18]=2[CH3:30])=[O:22])[CH:14]=[CH:19][CH:18]=[CH:30][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 22570191Benzyl 4-(3-chlorophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylate

Product 1

HCID 207589254-(3-Chlorophenyl)-3-ethoxycarbonyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3,3-diphenylpropyl)amide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10 ml of pyridine was added to a mixture of 512 mg (1.38 mmol) of benzyl 4-(3-chlorophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylate and 180 mg (1.66 mmol) of ethyl chloroformate, and they were stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, then washed with water and saturated aqueous sodium chloride solution and concentrated under reduced pressure. The product was dissolved in a mixture of 5 ml of methanol and 5 ml of THF. 3 N hydrochloric acid was added to the obtained solution, and they were stirred at room temperature for 10 minutes. After the concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate and then washed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1) to obtain the crude title compound.

Workup

  1. washwashed with water and saturated aqueous sodium chloride solution
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe product was dissolved in a mixture of 5 ml of methanol and 5 ml of THF
  4. addition3 N hydrochloric acid was added to the obtained solution, and they
  5. stirringwere stirred at room temperature for 10 minutes
  6. concentrationAfter the concentration under reduced pressure
  7. additionthe reaction mixture was diluted with ethyl acetate
  8. washwashed with 1 N hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=10/1 to 1/1)

Sources & evidence

ORD record
ord-ec8766218c474afca8958342d0002960
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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