Potassium Iodide → 8-(2,6-Difluorobenzyl)-5,8-dihydro-3-methyl-5-oxo-2-phenylimidazo[1,2-a]pyrimidine-6-carboxylic acid ethyl ester

HRID 1062598Notes

Reaction equation

HRID 1062598 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[N:10]([C:13]([CH3:22])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=2)[C:11]=1[OH:12])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:29][C:30]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:31]=1[CH2:32]Cl.[I-].[K+]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:11](=[O:12])[N:10]2[C:13]([CH3:22])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:15]=[C:9]2[N:8]([CH2:32][C:31]2[C:30]([F:29])=[CH:37][CH:36]=[CH:35][C:34]=2[F:38])[CH:7]=1)=[O:5])[CH3:2]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5815702,6-Difluorobenzyl chlorideHCID 178469684HCID 178469684, compound

Product 1

HCID 98235988-(2,6-Difluorobenzyl)-5,8-dihydro-3-methyl-5-oxo-2-phenylimidazo[1,2-a]pyrimidine-6-carboxylic acid ethyl esterYield 90.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of the compound obtained in Example 1 (157 mg, 0.53 mmol) in DMF (15 ml), potassium carbonate (80 mg, 0.58 mmol), 2,6-difluorobenzyl chloride (103 mg, 0.64 mmol) and potassium iodide (44 mg, 0.26 mmol) are added, followed by stirring at about 15 to 25° C. for 1 hour and stirring under heating at 80° C. for 1 hour. The brownish white crystalline substance obtained by concentration under reduced pressure of the reaction mixture is dispensed to ethyl acetate (30 ml) and water (30 ml). The water layer is extracted with ethyl acetate (10 ml), and the organic layers are combined and dried over sodium sulfate, after which the solvent is distilled off under reduced pressure to yield a crude brownish white crystalline product (204 mg), which is then purified by flush column chromatography to yield a white crystal (146 mg, 65%).

Workup

  1. stirringstirring
  2. temperatureunder heating at 80° C. for 1 hour
  3. customThe brownish white crystalline substance obtained by concentration under reduced pressure of the reaction mixture
  4. extractionThe water layer is extracted with ethyl acetate (10 ml)
  5. dry with materialdried over sodium sulfate
  6. distillationafter which the solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-45fedd8cd88842819394e1a1f26f69dc
Source dataset
uspto-grants-2005_11
Patent number
US06962919B2

Reaction notes

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