2-Azido-9-(2-hydroxyethoxymethyl)adenine → 2,6-Diamino-9-(2-hydroxyethoxymethyl)purine

HRID 848079Notes

Reaction equation

HRID 848079 reaction equation
[N:1]([C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH2:13][O:14][CH2:15][CH2:16][OH:17])=[C:6]([NH2:18])[N:5]=1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH2:13][O:14][CH2:15][CH2:16][OH:17])=[C:6]([NH2:18])[N:5]=1

Participants

4

Reactant 1

HCID 205176782-Azido-9-(2-hydroxyethoxymethyl)adenine

Product 1

HCID 945882,6-Diamino-9-(2-hydroxyethoxymethyl)purine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-azido-9-(2hydroxyethoxymethyl)adenine (0.41 g) and 10% palladium on charcoal (80 mg) in ethanol (41 ml) was shaken under hydrogen at 50 psi for 3.5 hours. The catalyst was removed by filtration through a celite pad and washed thoroughly with ethanol and water. The solvent was removed by evaporation under reduced pressure giving a quantitative yield (0.37 g) of nearly pure (one spot on TLC) 2-amino-9-(2-hydroxyethoxymethyl)adenine, m.p. 183°-184° C. after recrystallization from n-propanol.

Workup

  1. customThe catalyst was removed by filtration through a celite pad
  2. washwashed thoroughly with ethanol and water
  3. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4f3eff8c299644d1bfcd7abae285d881
Source dataset
uspto-grants-1981_10
Patent number
US04294831

Reaction notes

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