Dimethylformamide → HCID 15332397, compound

HRID 1792045Notes

Reaction equation

HRID 1792045 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[NH:12][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](=[O:22])([O-])[O-].[K+].[K+].[C:25]([O:31][CH2:32]Cl)(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].CN(C)[CH:36]=[O:37]>C(OCC)(=O)C>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH2:32][O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[C:13](=[O:18])[N:12]([CH2:19][O:22][C:36](=[O:37])[C:2]([CH3:7])([CH3:3])[CH3:1])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 125005077-Benzyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 15332397HCID 15332397, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

7-Benzylxanthine (9.54 g) was dissolved in N,N-dimethylformamide (250 ml), and potassium carbonate (17 g) and chloromethyl pivalate (14.2 ml) were added thereto. The reaction solution was stirred at 50° C. overnight, then diluted with ethyl acetate, and washed with water and 1 N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation. The residue was purified by silica gel chromatography to obtain 12.8 g of the title compound from a fraction eluted with hexane-ethyl acetate (3:2).

Workup

  1. washwashed with water and 1 N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed by distillation
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b65da21e126f4f65b15f36373117b212
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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