Hydrochloric Acid → HCID 178501792, compound

HRID 2354849Notes

Reaction equation

HRID 2354849 reaction equation
[Na].[CH2:2]([N:9]1[C:17](Br)=[N:16][C:15]2[C:10]1=[N:11][C:12]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[N:13][C:14]=2[NH2:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.C[OH:28]>>[CH2:2]([N:9]1[C:17]([OH:28])=[N:16][C:15]2[C:10]1=[N:11][C:12]([O:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[N:13][C:14]=2[NH2:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5360545SodiumHCID 23079479HCID 23079479, compound

Product 1

HCID 178501792HCID 178501792, compound

Procedure

After sodium (0.30 g, 13.04 mmol) was dissolved in methanol (30 ml), thereto was added 9-benzyl-8-bromo-2-methoxycarbonylmethoxyadenine (0.10 g, 0.25 mmol) obtained by Reference example 21, and the mixture was refluxed for 7 hours under stirring. After being allowed to cool, the solution was neutralized with concentrated hydrochloric acid and concentrated. After the residue was dissolved in methanol (30 ml), thereto was added sulfuric acid (2 ml) and the solution was stirred for 7 hours. After being neutralized in an ice bath with saturated sodium hydrogencarbonate solution, the solution was extracted with chloroform. 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˜30/1) and the obtained compound was washed with methanol to give the captioned compound (62 mg, 0.19 mmol) as a white solid.

Workup

  1. customobtained by Reference example 21
  2. temperaturethe mixture was refluxed for 7 hours
  3. temperatureto cool
  4. concentrationconcentrated
  5. dissolutionAfter the residue was dissolved in methanol (30 ml)
  6. additionwas added sulfuric acid (2 ml)
  7. stirringthe solution was stirred for 7 hours
  8. customAfter being neutralized in an ice bath with saturated sodium hydrogencarbonate solution
  9. extractionthe solution was extracted with chloroform
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. customThe residue was purified by column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=100/1˜30/1)
  13. washthe obtained compound was washed with methanol

Sources & evidence

ORD record
ord-a7935da4835a4a768203cee472d761e9
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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