Dimethylformamide → 8-{1-[1-(4-Isopropyl-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazol-4-yl}-7-methyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione

HRID 889067Notes

Reaction equation

HRID 889067 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([CH2:16][N:17]3[CH:21]=[C:20]([C:22]4[NH:30][C:29]5[C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH3:34])[C:26](=[O:35])[N:25]([CH2:36][CH2:37][CH3:38])[C:24]=5[N:23]=4)[CH:19]=[N:18]3)[CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:39](=O)([O-])[O-].[K+].[K+].CI.CN(C=O)C>O>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([CH2:16][N:17]3[CH:21]=[C:20]([C:22]4[N:30]([CH3:39])[C:29]5[C:28](=[O:31])[N:27]([CH2:32][CH2:33][CH3:34])[C:26](=[O:35])[N:25]([CH2:36][CH2:37][CH3:38])[C:24]=5[N:23]=4)[CH:19]=[N:18]3)[CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57988759HCID 57988759, compound

Product 1

HCID 579888008-{1-[1-(4-Isopropyl-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazol-4-yl}-7-methyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dioneYield 85.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8-{1-[1-(4-Isopropyl-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazol-4-yl}-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (0.030 g, 0.057 mmol), potassium carbonate (0.016 g, 0.115 mmol), methyl iodide (0.0039 ml, 0.0639 mmol) and DMF (1 ml) was heated at 50° C. for 20 hour. The mixture was cooled to room temperature and diluted with water (10 ml). The aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine solution, and dried over Na2SO4. The solvent was evaporated and the residue obtained was triturated with hexane to obtain the title compound (0.026 g, 84%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine solution
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue obtained
  7. customwas triturated with hexane

Sources & evidence

ORD record
ord-018022add44c4fcb85a668c79daaa1e9
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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