Potassium Carbonate → 2,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

HRID 1792057Notes

Reaction equation

HRID 1792057 reaction equation
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:6](=[O:20])[N:5]([CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]([CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[C:9]2[C:8](=[O:11])[N:7]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:6](=[O:20])[N:5]([CH2:21][O:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 235368892,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

Product 1

HCID 235368912,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-7-(3-methylbut-2-enyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylpropionic acid [8-chloro-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (600 mg) and potassium carbonate (630 mg) were suspended in N,N-dimethylformamide (10 ml), and 4-bromo-2-methyl-2-butene (183 μl) was added to the suspension at room temperature. After the reaction mixture was stirred at room temperature for 24 hours, the mixture was diluted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. After the solvent was removed by distillation from the organic layer, the residue was purified by silica gel column chromatography to give 470 mg of the title compound from the elution fraction of hexane-ethyl acetate (3:1).

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customAfter the solvent was removed by distillation from the organic layer
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-29e4af81ff0c42398af262e4cec2dd03
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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