Sodium Azide → 9-(3-Azidopropyl)adenine

HRID 1896066Notes

Reaction equation

HRID 1896066 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:2][CH2:3][CH2:4][N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[NH2:14])=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2865919-(3-chloropropyl)-9H-purin-6-amine

Product 1

HCID 120978459-(3-Azidopropyl)adenine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 9-(3-chloropropyl)adenine and sodium azide in DMF was stirred at 80° C. for 24 hours, cooled to room temperature and filtered. The solid was washed with CH2Cl2. The solvent was removed from the combined filtrates and the residue was taken up in water with sonication. The aqueous layer was extracted with CH2Cl2. After removing the solvent, the crude product was recrystallized from ethanol to give 9-(3-azidopropyl)adenine as a white crystalline solid.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe solid was washed with CH2Cl2
  4. customThe solvent was removed from the combined filtrates
  5. customthe residue was taken up in water with sonication
  6. extractionThe aqueous layer was extracted with CH2Cl2
  7. customAfter removing the solvent
  8. customthe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-dc8e8747d9b6443687f6f629e49ca7d3
Source dataset
uspto-grants-2013_08
Patent number
US08518885B2

Reaction notes

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