Water → HCID 59299565, compound

HRID 2386627Notes

Reaction equation

HRID 2386627 reaction equation
[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:4]=2[N:3]=1.CI.[C:26](=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[N:7]([CH3:26])[C:6](=[O:15])[N:5]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:21])([CH3:23])[CH3:22])[C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59299593HCID 59299593, compound

Product 1

HCID 59299565HCID 59299565, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-chloro-7-(2-propen-1-yl)-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3,7-dihydro-1H-purine-2,6-dione (3.14 g, 8.82 mmol) in DMF (50 ml) was added methyl iodide (0.659 ml, 10.58 mmol) and caesium carbonate (3.45 g, 10.58 mmol) and the reaction mixture stirred overnight at room temperature. The reaction mixture was partioned between water and ethyl acetate. The organic extract was separated, washed with brine, dried (MgSO4) and concentrated to afford the title compound 2.99 g (92%); m/z 388 [MH+].

Workup

  1. extractionThe organic extract
  2. customwas separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-406d25e11f3e4997ade9eec5efb997ed
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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