Sodium Cyanide → HCID 178510889, compound

HRID 2354843Notes

Reaction equation

HRID 2354843 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([N:11]1[C:19]([OH:20])=[N:18][C:17]2[C:12]1=[N:13][C:14]([CH2:22]Cl)=[N:15][C:16]=2[NH2:21])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C=O)C>[CH2:4]([N:11]1[C:19]([OH:20])=[N:18][C:17]2[C:12]1=[N:13][C:14]([CH2:22][C:1]#[N:2])=[N:15][C:16]=2[NH2:21])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 178508406HCID 178508406, compound

Product 1

HCID 178510889HCID 178510889, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °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. customAfter removing the solvent
  2. additionthe residue was poured into water
  3. extractionThe solution was extracted with dichloromethane
  4. dry with materialthe 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)
  7. washwashed with methanol

Sources & evidence

ORD record
ord-1cf6ceced06947c891e1c8fcb45e42ad
Source dataset
uspto-grants-2010_07
Patent number
US07754728B2

Reaction notes

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