Acetic Acid → 9-(2-Hydroxyethyl)-9H-purin-6-ol

HRID 27582Notes

Reaction equation

HRID 27582 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH2:12][OH:13].[OH-].[Na+].C(O)(=[O:18])C>O>[OH:13][CH2:12][CH2:11][N:6]1[CH:5]=[N:4][C:3]2[C:2](=[O:18])[NH:10][CH:9]=[N:8][C:7]1=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 2340102-(6-Chloro-9h-purin-9-yl)ethanol

Product 1

HCID 1354085819-(2-Hydroxyethyl)-9H-purin-6-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Chloro-9-hydroxyethyl purine, III (4 g), was added slowly to warm N NaOH (30 ml) and refluxed for 2 hr. The reaction is cooled in ice and neutralized with glacial acetic acid. After filtration, portions of unreacted III are removed. The product is recrystallized from methanol and washed with acetone. Colorless crystals. Yield, 1 g. (28%) mp. 274°; uv (H2O, pH 5.5), λmax 250 nm.

Workup

  1. temperaturerefluxed for 2 hr
  2. filtrationAfter filtration, portions of unreacted III
  3. customare removed
  4. customThe product is recrystallized from methanol
  5. washwashed with acetone
  6. customYield

Sources & evidence

ORD record
ord-5dfd6319591e4abe8a86c156ccd56b0e
Source dataset
uspto-grants-1980_09
Patent number
US04221910

Reaction notes

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