Sodium hydride → [7-Benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate

HRID 1792053Notes

Reaction equation

HRID 1792053 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.[H-].[Na+].[C:21]([O:27][CH2:28]Cl)(=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH2:28][O:27][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[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 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 125005077-Benzyl-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 15332398[7-Benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Benzylxanthine (8.66 g) was dissolved in N,N-dimethylformamide (300 ml); sodium hydride (1.57 g) and chloromethyl pivalate (7.7 ml) were added to the solution; and the mixture was stirred at room temperature 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 and filtered. Then, the solvent was removed by distillation. The residue was purified by silica gel column chromatography to give 2.66 g of the title compound from the elution fraction of hexane-ethyl acetate 1:1.

Workup

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

Sources & evidence

ORD record
ord-2e6f7aa19885484f959104b2374be228
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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