Dimethylformamide → HCID 15332397, compound

HRID 501372Notes

Reaction equation

HRID 501372 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>[CH3:27][C:26]([CH3:29])([CH3:28])[C:25]([O:31][CH2:32][N:14]1[C:15](=[O:17])[C:16]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=[N:10][C:11]=2[N:12]([CH2:19][O:22][C:36](=[O:37])[C:2]([CH3:7])([CH3:3])[CH3:1])[C:13]1=[O:18])=[O:30]

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

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

Workup

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

Sources & evidence

ORD record
ord-113512596ed74ab7b9887bfdfcfcd6f4
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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