Dimethylformamide → 3-phenyl-5,7-dimethyl-1-(4-bromobutyl)pyrido[2,3-d]-pyrimidin-2,4(1H,3H)-dione

HRID 1905016Notes

Reaction equation

HRID 1905016 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[C:14]([CH3:19])=[CH:15][C:16]([CH3:18])=[N:17][C:10]=3[NH:9][C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]1([N:7]2[C:12](=[O:13])[C:11]3[C:14]([CH3:19])=[CH:15][C:16]([CH3:18])=[N:17][C:10]=3[N:9]([CH2:25][CH2:24][CH2:23][CH2:22][Br:21])[C:8]2=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 200370183-phenyl-5,7-dimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 140104403-phenyl-5,7-dimethyl-1-(4-bromobutyl)pyrido[2,3-d]-pyrimidin-2,4(1H,3H)-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising of 13.36 g 3-phenyl-5,7-dimethylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione, 43.18 g of 1,4-dibromobutane, 10.37 g of anhydrous potassium carbonate and 150 ml of N,N-dimethyl-formamide was heated at 80° C. for 3 hours. After the completion of the reaction, the reaction mixture was poured into 600 ml of water. The resulting mixture was extracted with ethyl acetate and further with a small amount of dichloromethane. These extracts were combined, dried over anhydrous potassium carbonate and distilled under a reduced pressure to remove the solvent. The obtained residue was dissolved in a small amount of dichloromethane, columnchromatographed over silica gel column and eluted with dichloromethane. The eluate was concentrated under a reduced pressure and the residue was recrystallized from a dichloromethaneisopropyl ether solvent to give 13.06 g of 3-phenyl-5,7-dimethyl-1-(4-bromobutyl)pyrido[2,3-d]-pyrimidin-2,4(1H,3H)-dione having a melting point of 153.5° to 154.5° C., which serves as an intermediate (yield: 65%).

Workup

  1. customAfter the completion of the reaction
  2. extractionThe resulting mixture was extracted with ethyl acetate and further with a small amount of dichloromethane
  3. dry with materialdried over anhydrous potassium carbonate
  4. distillationdistilled under a reduced pressure
  5. customto remove the solvent
  6. dissolutionThe obtained residue was dissolved in a small amount of dichloromethane
  7. washeluted with dichloromethane
  8. concentrationThe eluate was concentrated under a reduced pressure
  9. customthe residue was recrystallized from a dichloromethaneisopropyl ether solvent

Sources & evidence

ORD record
ord-01f6c609413f4d099f4e4d7465d7a8d8
Source dataset
uspto-grants-1989_06
Patent number
US04841051

Reaction notes

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