1,4-Dibromobutane → 9-(4-Bromobutyl)-2-butoxy-8-methoxyadenine

HRID 905616Notes

Reaction equation

HRID 905616 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[Br:31][CH2:32][CH2:33][CH2:34][CH2:35]Br>CN(C)C=O.[Cl-].[Na+].O>[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][N:19]1[C:18]([O:22][CH3:23])=[N:17][C:16]2[C:20]1=[N:21][C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])=[N:14][C:15]=2[NH2:24]

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 178450370HCID 178450370, compound

Product 1

HCID 231585119-(4-Bromobutyl)-2-butoxy-8-methoxyadenine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The compound obtained in Example 2-1 step (v) (0.5 g) was added to potassium carbonate (0.92 g) and 1,4-dibromobutane (0.85 ml) in dimethylformamide (5 ml), and the mixture was stirred at room temperature for 16 hours. To the reaction solution was added brine and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and concentrated to dryness. The residue was purified by flash column chromatography (ethyl acetate) to give the titled compound, as a white solid. Yield: 370 mg (70%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b6bc47f6cd834c0fb2b60d17034d6c30
Source dataset
uspto-grants-2011_09
Patent number
US08012964B2

Reaction notes

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