1-(1-Ethylpropyl)-6-mesityl-4,8-dimethyl-2,3-dihydro-1H-imidazo[1,5-a]pyrrolo[3,2-e]pyrimidine → 1-(1-Ethylpropyl)-6-mesityl-4,8-dimethyl-1H-imidazo[1,5-a]pyrrolo[3,2-e]primidine

HRID 966045Notes

Reaction equation

HRID 966045 reaction equation
[CH2:1]([CH:3]([N:6]1[C:14]2[N:13]3[C:15]([CH3:27])=[N:16][C:17]([C:18]4[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=4[CH3:26])=[C:12]3[N:11]=[C:10]([CH3:28])[C:9]=2[CH2:8][CH2:7]1)[CH2:4][CH3:5])[CH3:2]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH2:1]([CH:3]([N:6]1[C:14]2[N:13]3[C:15]([CH3:27])=[N:16][C:17]([C:18]4[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=4[CH3:26])=[C:12]3[N:11]=[C:10]([CH3:28])[C:9]=2[CH:8]=[CH:7]1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 222495281-(1-Ethylpropyl)-6-mesityl-4,8-dimethyl-2,3-dihydro-1H-imidazo[1,5-a]pyrrolo[3,2-e]pyrimidine

Product 1

HCID 208213101-(1-Ethylpropyl)-6-mesityl-4,8-dimethyl-1H-imidazo[1,5-a]pyrrolo[3,2-e]primidineYield 39.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

Manganese dioxide (67 mg, 0.77 mmol) was added to a solution of 1-(1-ethylpropyl)-6-mesityl-4,8-dimethyl-2,3-dihydro-1H-imidazo[1,5-a]pyrrolo[3,2-e]pyrimidine (58 mg, 0.15 mmol) in toluene (10 mL), followed by heating under reflux for three days. After filtering through Celite, the mixture was evaporated. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane), to give the title compound (22 mg) as pale yellow crystals.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for three days
  3. filtrationAfter filtering through Celite
  4. customthe mixture was evaporated
  5. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-77f4bad9e6bc4be7bc6e8c2891d5f8ad
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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