Hydrochloric Acid → HCID 178499630, compound

HRID 1684979Notes

Reaction equation

HRID 1684979 reaction equation
[CH2:1]([N:8]1[C:16]([OH:17])=[N:15][C:14]2[C:9]1=[N:10][C:11]([CH2:19][C:20]#N)=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:22].[Na+].Cl.[CH3:25][OH:26]>>[CH2:1]([N:8]1[C:16]([OH:17])=[N:15][C:14]2[C:9]1=[N:10][C:11]([CH2:19][C:20]([O:26][CH3:25])=[O:22])=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 178510889HCID 178510889, compound

Product 1

HCID 178499630HCID 178499630, compound

Conditions

Temperature
60 °C

Procedure

After sodium cyanide (0.20 g, 4.08 mmol) and 9-benzyl-2-chloromethyl-8-hydroxyadenine (0.20 g, 0.69 mmol) were added to DMF (10 ml), the mixture was stirred at 80° C. for 7 hours. After removing the solvent, the residue was poured into water and the solution was neutralized with concentrated hydrochloric acid. The solution was extracted with dichloromethane, and 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 9-benzyl-2-cyanomethyl-8-hydroxyadenine (0.16 g, 0.57 mmol) as a pale yellow solid. Thus obtained 9-benzyl-2-cyanomethyl-8-hydroxyadenine (0.08 g, 0.29 mmol) was added to a mixed solvent of 5% sodium hydroxide solution (20 ml) and methanol (10 ml), and the mixture was stirred at 60° C. for 8 hours. After the mixture was neutralized with concentrated hydrochloric acid, the solvent was removed. The residue and sulfuric acid (1 ml) were added to methanol (50 ml), and the mixture was refluxed for 3 hours under stirring. After being neutralized with saturated sodium hydrogencarbonate solution in an ice bath, the solution was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=100/1˜30/1) and washed with methanol to give the captioned compound (0.02 g, 0.06 mmol) as a white solid.

Workup

  1. customthe solvent was removed
  2. additionThe residue and sulfuric acid (1 ml) were added to methanol (50 ml)
  3. temperaturethe mixture was refluxed for 3 hours
  4. stirringunder stirring
  5. customAfter being neutralized with saturated sodium hydrogencarbonate solution in an ice bath
  6. extractionthe solution was extracted with dichloromethane
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified with column chromatography (SiO2 20 g, eluting solvent: CHCl3/MeOH=100/1˜30/1)
  10. washwashed with methanol

Sources & evidence

ORD record
ord-9e29de4260f74280b93e7a6f55e88cb0
Source dataset
uspto-grants-2012_04
Patent number
US08148371B2

Reaction notes

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