Citric Acid → HCID 23018274, compound

HRID 1348554Notes

Reaction equation

HRID 1348554 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.Cl[C:11]1[N:16]2[CH:17]=[CH:18][N:19]=[C:15]2[N:14]=[C:13]([Cl:20])[C:12]=1[C:21]1[C:26]([F:27])=[CH:25][C:24]([F:28])=[CH:23][C:22]=1[F:29].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(Cl)(Cl)Cl>[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:11]2[N:16]3[CH:17]=[CH:18][N:19]=[C:15]3[N:14]=[C:13]([Cl:20])[C:12]=2[C:21]2[C:26]([F:27])=[CH:25][C:24]([F:28])=[CH:23][C:22]=2[F:29])[N:5]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 62103,5-DimethylpyrazoleHCID 24758Sodium hydrideHCID 230182755,7-Dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine

Product 1

HCID 23018274HCID 23018274, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Into a mixture of 0.040 g of sodium hydride (60% in oil) and 2 ml of tetrahydrofuran, a solution of 0.096 g of 3,5-dimethylpyrazole in 3 ml of tetrahydrofuran was added dropwise. The mixture was added to a solution of 0.32 g of 5,7-dichloro-6-(2,4,6-trifluorophenyl)imidazo[1,2-a]pyrimidine in 5 ml of tetrahydrofuran under ice-cooling. To the reaction mixture, chloroform and aqueous citric acid solution were added. The separated organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 0.18 g of 5-(3,5-dimethylpyrazol-1-yl)-6-(2,4,6-trifluorophenyl)-7-chloroimidazo[1,2-a]pyrimidine.

Workup

  1. temperaturecooling
  2. washThe separated organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b8fc64842d254a7a9cabb6ac7f48d28c
Source dataset
uspto-grants-2007_05
Patent number
US07211545B2

Reaction notes

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