Hydrogen iodide → 9-(1-Hydroxy-2-propyl)-6-iodopurine

HRID 27443

Reaction equation

HRID 27443 reaction equation
[OH:1][CH2:2][CH:3]([N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2Cl)[CH3:4].[IH:15]>O>[OH:1][CH2:2][CH:3]([N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][CH:8]=[N:9][C:10]=2[I:15])[CH3:4]

Participants

4

Reactant 2

HCID 24841Hydrogen iodideHCID 4540192-(6-Chloropurin-9-yl)propan-1-ol

Product 1

HCID 233429069-(1-Hydroxy-2-propyl)-6-iodopurine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

9-(1-Hydroxy-2-propyl)-6-chloropurine (I, 1.5 g, 7 mmol) was added to hydroiodic acid (15 ml) at -10° with stirring for 45 min. The precipitate was filtered, neutralized with anhydrous sodium acetate at 5°, and washed with a little cold water (3 times). Recrystallization from ethanol/H2O, gave colorless crystals. Yield=0.9 g (42%) mp=193°-194° uv λmax 276 nm (H2O, pH 5.5).

Workup

  1. filtrationThe precipitate was filtered
  2. customneutralized with anhydrous sodium acetate at 5°
  3. washwashed with a little cold water (3 times)
  4. customRecrystallization from ethanol/H2O
  5. customgave colorless crystals

Sources & evidence

ORD record
ord-9dfef0452a764a4b8d5f42cfbdf0f424
Source dataset
uspto-grants-1980_09
Patent number
US04221794

Linked notes

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