Ethanol → HCID 20517686, compound

HRID 2198920Notes

Reaction equation

HRID 2198920 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][O:8][CH2:9][N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH2:19])C(=O)C2=CC=CC=C12.O.NN.C(O)C>COCCO>[NH2:5][CH2:6][CH2:7][O:8][CH2:9][N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][CH:13]=[N:14][C:15]=2[NH2:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 20517684HCID 20517684, compound

Product 1

HCID 20517686HCID 20517686, compoundYield 48.1%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 9-(2-phthalimidoethoxymethyl)adenine (3.38 g), hydrazine hydrate (1.0 ml of an 85% aqueous solution) and ethanol (150 ml) was heated at reflux for 2 hours. 2-Methoxyethanol (50 ml) was added and refuxing continued for an additional 2 hours. The solvent was removed under reduced pressure and 1 N hydrochloric acid (50 ml) added. The mixture was stirred at ambient temperature for 30 minutes and allowed to stand at 0° C. overnight. The solution was filtered and the filtrate diluted with water (100 ml) and stirred with excess basic ion exchange resin (Rexyn 201(OH)) until a negative silver nitrate test was obtained. It was then filtered and most of the water removed under reduced pressure. The aqueous solution was cooled and the resulting solid removed by filtration. This was recrystallized from isopropanol to give 9-(2-aminoethoxymethyl)adenine (1.0 g), m.p. 170°-171° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed under reduced pressure and 1 N hydrochloric acid (50 ml)
  4. additionadded
  5. waitto stand at 0° C. overnight
  6. filtrationThe solution was filtered
  7. additionthe filtrate diluted with water (100 ml)
  8. stirringstirred with excess basic ion exchange resin (Rexyn 201(OH)) until a negative silver nitrate test
  9. customwas obtained
  10. filtrationIt was then filtered and most of the water
  11. customremoved under reduced pressure
  12. temperatureThe aqueous solution was cooled
  13. customthe resulting solid removed by filtration
  14. customThis was recrystallized from isopropanol

Sources & evidence

ORD record
ord-24e860e85b0b485d98704d3f8923d970
Source dataset
uspto-grants-1982_11
Patent number
US04360522

Reaction notes

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