Potassium Permanganate → 6-Tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2,6-dicarboxylate

HRID 1868457Notes

Reaction equation

HRID 1868457 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[N:14]2[CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:13]2[NH:12][C:11]([CH3:23])=[C:10]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].[O-][Mn](=O)(=O)=O.[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]2[CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:13]2[N:12]=[C:11]([CH3:23])[C:10]=1[C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 469017426-Tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate

Product 1

HCID 469017436-Tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2,6-dicarboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (191 mg, 0.42 mmol) in acetone (5 mL) was added KMnO4 (66 mg, 0.42 mmol). After 1 h, the reaction was filtered through celite and concentrated under reduced pressure. The resulting residue was diluted with CH2Cl2 and extracted with H2O (2×). The organic layer was dried over MgSO4, concentrated under reduced pressure and recrystallized from EtOAc to obtain 6-tert-butyl 2-ethyl 5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2,6-dicarboxylate (107 mg, 57%) as white crystals.

Workup

  1. filtrationthe reaction was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting residue was diluted with CH2Cl2
  4. extractionextracted with H2O (2×)
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customrecrystallized from EtOAc

Sources & evidence

ORD record
ord-691c318a35eb402ca92f538a3c4bb102
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

Loading…