Hydrochloric Acid → HCID 178450374, compound

HRID 2354838Notes

Reaction equation

HRID 2354838 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([OH:35])[N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH2:25][CH2:26][O:27]CC3C=CC=CC=3)=[O:23])[CH:17]=2)=[C:8]([NH2:36])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.C1COCC1>[Pd].CO>[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([OH:35])[N:12]2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([O:24][CH2:25][CH2:26][OH:27])=[O:23])[CH:17]=2)=[C:8]([NH2:36])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 178450375HCID 178450375, compound

Product 1

HCID 178450374HCID 178450374, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Butoxy-8-hydroxy-9-{3-(2-benzyloxyethoxycarbonyl)benzyl}adenine (0.03 g, 0.06 mmol) obtained by Example 5, 5% Pd/C (60 mg) and concentrated hydrochloric acid (0.1 ml) were added to a mixed solvent of THF (30 ml) and methanol (30 ml), and the mixture was stirred under hydrogen atmosphere at room temperature for 60 hours. The reaction mixture was filtered, neutralized with saturated sodium hydrogencarbonate solution and extracted with dichloromethane. The 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) and washed with methanol to give the captioned compound (0.01 g, 0.02 mmol, yield: 42%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH 100/1˜50/1)
  6. washwashed with methanol

Sources & evidence

ORD record
ord-fe1cb36689164e78bd567416c17a3e27
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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