2-Chloro-9-(2-hydroxyethoxymethyl)adenine → 2-Chloro-9-(2-hydroxyethoxymethyl)hypoxanthine

HRID 1577089Notes

Reaction equation

HRID 1577089 reaction equation
N([O-])=[O:2].[Na+].[Cl:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH2:15][O:16][CH2:17][CH2:18][OH:19])=[C:8](N)[N:7]=1>C(O)(=O)C>[Cl:5][C:6]1[NH:7][C:8](=[O:2])[C:9]2[N:10]=[CH:11][N:12]([CH2:15][O:16][CH2:17][CH2:18][OH:19])[C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 128995862-Chloro-9-(2-hydroxyethoxymethyl)adenineHCID 23668193Sodium Nitrite

Product 1

HCID 1356751292-Chloro-9-(2-hydroxyethoxymethyl)hypoxanthineYield 49.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Solid sodium nitrite (0.97 g) was added at room temperature with stirring over a period of one hour to a solution of 2-chloro-9-(2-hydroxyethoxymethyl)adenine (0.5 g) in glacial acetic acid (10 ml). The reaction mixture was stirred for an additional 41/2 hours. The white solid was removed by filtration, washed with cold acetic acid and then well triturated with cold water to remove the sodium acetate present. The solid product was retained. The combined acetic acid filtrate and wash was evaporated at reduced pressure and 40° C. bath temperature and the residual oil triturated with cold water. The resulting solid material was combined with the previously isolated solid and the combined solids dried and recrystallized from ethanol to give 2-chloro-9-(2-hydroxyethoxymethyl) hypoxanthine (0.25 g), m.p. >310° C. Elemental analysis and NMR spectrum were consistent with this structure.

Workup

  1. customThe white solid was removed by filtration
  2. washwashed with cold acetic acid
  3. customwell triturated with cold water
  4. customto remove the sodium acetate present
  5. washThe combined acetic acid filtrate and wash
  6. customwas evaporated at reduced pressure and 40° C. bath temperature
  7. customthe residual oil triturated with cold water
  8. customthe combined solids dried
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a0fb22c18e8a46eda4885bd396d3f488
Source dataset
uspto-grants-1981_09
Patent number
US04287188

Reaction notes

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