Acetic Acid → 2-(2-{1-[1-(1-Benzyl-4,5-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethyl)-isoindole-1,3-dione

HRID 1374873Notes

Reaction equation

HRID 1374873 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[N:10]=[C:9]1[CH:17]([N:21]([CH2:31][C:32](=O)[CH2:33][CH2:34][N:35]1C(=O)C2C(=CC=CC=2)C1=O)[C:22](=O)[C:23]1C=CC(C)=[CH:25][CH:24]=1)[CH:18]([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:47]([O-:50])(=O)[CH3:48].[NH4+:51].[C:52]([OH:55])(=O)[CH3:53]>>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[N:10]=[C:9]1[CH:17]([N:21]1[CH:31]=[C:32]([CH2:33][CH2:34][N:35]2[C:47](=[O:50])[C:48]3[C:53](=[CH:1][CH:2]=[CH:3][CH:4]=3)[C:52]2=[O:55])[N:51]=[C:22]1[C:23]1[CH:24]=[CH:25][C:12]([CH3:13])=[CH:11][CH:16]=1)[CH:18]([CH3:19])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 21076932N-[1-(1-Benzyl-4,5-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-N-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-butyl]-4-methyl-benzamide

Product 1

HCID 210769262-(2-{1-[1-(1-Benzyl-4,5-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethyl)-isoindole-1,3-dioneYield 38%

Procedure

To N-[1-(1-Benzyl-4,5-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-N-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-butyl]-4-methyl-benzamide (0.884 g, 1.62 mmol) in glacial acetic acid (15 mL) was added ammonium acetate (6.22 g, 80.8 mmol) and the reaction was heated at reflux for 16 h. The reaction was concentrated in vacuo and the residue was basified with saturated NaHCO3, extracted into EtOAc, washed with water and brine, dried (Na2SO4), and evaporated to dryness. The residue was purified by flash chromatography on silica gel (3:1 EtOAc:hexanes) to give the title compound as a pale yellow foam (0.371 g, 38%). MS(ES+) m/c 600 [M+H]+.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 16 h
  3. concentrationThe reaction was concentrated in vacuo
  4. extractionextracted into EtOAc
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography on silica gel (3:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-c760f22bf5564f578e88b3ace4b39538
Source dataset
uspto-grants-2007_01
Patent number
US07166595B2

Reaction notes

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