Ethyl bromoacetate → HCID 23079434, compound

HRID 2354841Notes

Reaction equation

HRID 2354841 reaction equation
[Br:1][C:2]1[N:3]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:5]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C>[Br:1][C:2]1[N:3]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:22][CH:23]=2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[N:5]=2

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 23079438HCID 23079438, compound

Product 1

HCID 23079434HCID 23079434, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Bromo-2-butoxy-9-(4-acetoxybenzyl)adenine (0.29 g, 0.67 mmol) obtained in accordance with the method of Reference example 4 was added to methanol (10 ml) and 5% sodium hydroxide solution (10 ml), and the mixture was stirred at room temperature for 4 hours. After the mixture was neutralized with concentrated hydrochloric acid, the resulting solid was filtered and washed with methanol to give 8-bromo-2-butoxy-9-(4-hydroxybenzyl)adenine (0.19 g, 0.49 mmol, yield: 73%) as a white solid. Thus obtained 8-bromo-2-butoxy-9-(4-hydroxybenzyl)adenine (0.05 g, 0.13 mmol) and potassium carbonate (0.02 g, 0.14 mmol) were added to DMF (10 ml), and then thereto was added ethyl bromoacetate (0.04 g, 0.24 mmol). The mixture was stirred at room temperature for 18 hours. After removing the solvent, the residue was poured into water and extracted with dichloromethane. The combined organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=100/1˜50/1) to give 8-bromo-2-butoxy-9-(4-ethoxycarbonylmethoxybenzyl)adenine (0.06 g, 0.12 mmol, yield: 96%) as a white solid. And then the captioned compound was obtained in accordance with the method of Example 1, Yield: 80%.

Workup

  1. customAfter removing the solvent
  2. additionthe residue was poured into water
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=100/1˜50/1)

Sources & evidence

ORD record
ord-96f437948be64709aadd9e7274a245f4
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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