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

HRID 27442Notes

Reaction equation

HRID 27442 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-b0a609ba16bd454eb299c1dd1a0801c2
Source dataset
uspto-grants-1980_09
Patent number
US04221794

Reaction notes

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