Water → 9-((2-Acetoxyethoxy)methyl)-6-chloropurine

HRID 865358

Reaction equation

HRID 865358 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[H-].[Na+].[C:13]([O:16][CH2:17][CH2:18][O:19][CH2:20]Br)(=[O:15])[CH3:14].O>CN(C=O)C>[C:13]([O:16][CH2:17][CH2:18][O:19][CH2:20][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][CH:9]=[N:10][C:2]=2[Cl:1])(=[O:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3676562-(Bromomethoxy)ethyl acetateHCID 53592776-Chloropurine

Product 1

HCID 5126559-((2-Acetoxyethoxy)methyl)-6-chloropurineYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloropurine (6 g, 38.8 mmoles) in DMF was added sodium hydride 60% (0.93 g) over 1.5 hour period. (2-acetoxyethoxy)methyl bromide was then added at room temperature; the reaction mixture was allowed to stir for 2 hours under N2 atmosphere. H2O was added and the product was extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered, and evaporated in vacuo to give a light yellow solid 7.1 g, 68% yield of 9-[(2-Acetoxy-ethoxy)methyl]-6-chloro-purine. The crude was used without further purification.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-39ac5dc21a5743079ce8dd484cb442a2
Source dataset
uspto-grants-1996_10
Patent number
US05565566

Linked notes

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