Pyridine → [1-(2,2-Dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate

HRID 1792079Notes

Reaction equation

HRID 1792079 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].[CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)=[O:29].N1C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:22][C:20]([CH3:21])([CH3:23])[C:19]([O:18][CH2:17][N:9]1[C:10](=[O:16])[C:11]2[N:12]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH:28]=[O:29])[CH:13]=[N:14][C:15]=2[N:7]([CH2:6][O:5][C:3](=[O:4])[C:2]([CH3:27])([CH3:26])[CH3:1])[C:8]1=[O:25])=[O:24]

Participants

7

Reactant 3

HCID 1049PyridineHCID 2921892-Formylphenylboronic acidHCID 153324012,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester

Product 1

HCID 23536861[1-(2,2-Dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionateYield 31.7%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylpropionic acid [3-(2,2-dimethylpropionyloxymethyl)-2,6-dioxo-2,3,6,7-tetrahydropurin-1-yl]methyl ester (10.2 g), 2-formylphenylboronic acid (8.04 g), and copper(II) acetate (7.30 g) were suspended in N,N-dimethylformamide (50 ml), pyridine (4.34 ml) was added thereto, and the mixture was stirred at room temperature for 37 hours. The reaction mixture was diluted with ethyl acetate; and washed with water. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give 4.12 g of the title compound from the elution fraction of hexane-ethyl acetate (1:2).

Workup

  1. washand washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-05e81e29142c4ae0868982a133fee016
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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