Chlorosuccinimide → 2,2-Dimethylpropionic acid [8-chloro-1-(2,2-dimethyl-propionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester

HRID 1792080Notes

Reaction equation

HRID 1792080 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[C:3]([O:5][CH2:6][N:7]1[C:15](=[O:16])[C:14]2[N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH:23]=[O:24])[CH:12]=[N:11][C:10]=2[N:9]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C:8]1=[O:33])=[O:4].[Cl:36]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[Cl:36][C:12]1[N:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]=[O:24])[C:14]2[C:15](=[O:16])[N:7]([CH2:6][O:5][C:3](=[O:4])[C:2]([CH3:35])([CH3:34])[CH3:1])[C:8](=[O:33])[N:9]([CH2:25][O:26][C:27](=[O:32])[C:28]([CH3:29])([CH3:31])[CH3:30])[C:10]=2[N:11]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 23536861[1-(2,2-Dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate

Product 1

HCID 235368902,2-Dimethylpropionic acid [8-chloro-1-(2,2-dimethyl-propionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl esterYield 74.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylpropionic acid [1-(2,2-dimethylpropionyloxymethyl)-7-(2-formylphenyl)-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester (2.50 g) and N-chlorosuccinimide (896 mg) were dissolved in N,N-dimethylformamide (25 ml), and the mixture was stirred at room temperature for 8 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 2.0 g of the title compound from the elution fraction of hexane-ethyl acetate (2:1).

Workup

  1. washwashed 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-4827b0d3f5684e7292dc522efb21c879
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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