Potassium Carbonate → 6-chloro-1-(2'-cyanobiphenyl-4-yl)methyl-3-propylpyrimidine-2,4(1H,3H)-dione

HRID 373238Notes

Reaction equation

HRID 373238 reaction equation
[Cl:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[CH:3]=1.Cl[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]#[N:28])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:7]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]#[N:28])=[CH:19][CH:20]=2)[C:6](=[O:8])[N:5]([CH2:9][CH2:10][CH3:11])[C:4](=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6408466-chloro-3-propylpyrimidine-2,4(1H,3H)-dioneHCID 217117564'-(chloromethyl)-[1,1'-Biphenyl]-2-carbonitrile

Product 1

HCID 198115376-chloro-1-(2'-cyanobiphenyl-4-yl)methyl-3-propylpyrimidine-2,4(1H,3H)-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-3-propylpyrimidine-2,4(1H,3H)-dione (3 g), 4-chloromethyl-2'-cyanobiphenyl (4.76 g) and potassium carbonate (2.64 g) in DMF (50 ml) was stirred at room temperature for 3 hours and then at 60° C. for 2 hours. The reaction mixture was concentrated to dryness in vacuo and then the residue was dissolved in methylene chloride. The insoluble material was removed from the reaction mixture by filtration and the filtrate was concentrated to dryness. The resulting residue was purified by column chromatography on silica gel to give colorless crystals (5.9 g, 98%).

Workup

  1. waitat 60° C. for 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness in vacuo
  3. dissolutionthe residue was dissolved in methylene chloride
  4. customThe insoluble material was removed from the reaction mixture by filtration
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c446ae110285482c96bc7206d32408f3
Source dataset
uspto-grants-1992_11
Patent number
US05162326

Reaction notes

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