Sodium Iodide → 6-(2-Azidoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl) amide

HRID 24608Notes

Reaction equation

HRID 24608 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:14]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[NH:15][C:16](=[O:24])[NH:17][C:18]=2[CH2:19][O:20][CH2:21][CH2:22]Cl)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:32]=[N+:33]=[N-:34].[Na+].[I-].[Na+]>CN(C=O)C>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:14]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)[NH:15][C:16](=[O:24])[NH:17][C:18]=2[CH2:19][O:20][CH2:21][CH2:22][N:32]=[N+:33]=[N-:34])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 207588826-(2-Chloroethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl)amide

Product 1

HCID 207588806-(2-Azidoethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl) amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

180 mg (0.389 mmol) of 6-(2-chloroethoxymethyl)-4-(3-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid (3-phenylpropyl)amide was dissolved in 10 ml of DMF. 38.0 mg (0.584 mmol) of sodium azide and 58.3 mg (0.389 mmol) of sodium iodide were added to the obtained solution, and they were stirred at 60° C. for 2 days. After the concentration under reduced pressure, the reaction mixture was diluted with ethyl acetate and then washed with 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 (dichloromethane/methanol=100/1) to obtain the title compound.

Workup

  1. concentrationAfter the concentration under reduced pressure
  2. additionthe reaction mixture was diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol=100/1)

Sources & evidence

ORD record
ord-d9f131ed77a94f699f7abaefa36ddcfa
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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