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

HRID 1792054Notes

Reaction equation

HRID 1792054 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[N:12]([CH2:19][O:20][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.[C:27](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:27])[C:13](=[O:18])[N:12]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:25])[CH3:24])[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 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15332398[7-Benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate

Product 1

HCID 23536880[7-Benzyl-1-methyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionateYield 78.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylpropionic Acid [7-benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl ester (2.66 g) was dissolved in N,N-dimethylformamide (30 ml), potassium carbonate (1.6 g) and iodomethane (1 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 triturated with toluene to give 2.16 g of the title compound.

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 triturated with toluene

Sources & evidence

ORD record
ord-f381f558a9f34260820e392f41385c6b
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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