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

HRID 501367Notes

Reaction equation

HRID 501367 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][CH2:6][N:7]1[C:15]2[N:14]=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]=2[C:10](=[O:23])[NH:9][C:8]1=[O:24])=[O:4].[C:27](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]([CH3:26])([CH3:25])[C:3]([O:5][CH2:6][N:7]1[C:15]2[N:14]=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]=2[C:10](=[O:23])[N:9]([CH3:27])[C:8]1=[O:24])=[O:4]

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

2.66 g of [7-benzyl-2,6-dioxo-1,2,6,7-tetrahydropurin-3-yl]methyl 2,2-dimethylpropionate was dissolved in 30 ml of N,N-dimethylformamide, and 1.6 g of potassium carbonate and 1 ml of methyl iodide were added thereto. 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, then filtered. The solvent was evaporated under reduced pressure. The residue was triturated with toluene. Thus, 2.16 g of the title compound was obtained.

Workup

  1. washwashed with water and 1N hydrochloric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was triturated with toluene

Sources & evidence

ORD record
ord-3aff1e88711e40fb8dc54ef10e98020a
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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