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

HRID 1792064Notes

Reaction equation

HRID 1792064 reaction equation
[CH3:1][C:2]([CH3:27])([CH3:26])[C:3]([O:5][CH2:6][N:7]1[C:15]2[N:14]=[CH:13][NH:12][C:11]=2[C:10](=[O:16])[N:9]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C:8]1=[O:25])=[O:4].Br[CH2:29][C:30]#[C:31][CH3:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:29]([N:12]1[C:11]2[C:10](=[O:16])[N:9]([CH2:17][O:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:23])[CH3:22])[C:8](=[O:25])[N:7]([CH2:6][O:5][C:3](=[O:4])[C:2]([CH3:27])([CH3:26])[CH3:1])[C:15]=2[N:14]=[CH:13]1)[C:30]#[C:31][CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27568621-Bromo-2-butyneHCID 153324012,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

Product 1

HCID 695605412,2-Dimethylpropionic acid [7-(2-butynyl)-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,2-dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (1.0 g), 1-bromo-2-butyne (0.28 ml), anhydrous potassium carbonate (0.73 g), and N,N-dimethylformamide (15 ml) was stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using 20–30% ethyl acetate/hexane to give 1.06 g of 2,2-dimethylpropionic acid [7-(2-butynyl)-3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate-water
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f9322b3ac59c4ebe9c338cb97e2c4d5f
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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