Hydrochloric Acid → 2-Amino-9-(2-hydroxyethoxymethyl)adenine hydrochloride

HRID 2285555Notes

Reaction equation

HRID 2285555 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][OH:15])=[C:4]([NH2:16])[N:3]=1.[ClH:17].CCOCC>C(O)C>[ClH:17].[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][OH:15])=[C:4]([NH2:16])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 945882,6-Diamino-9-(2-hydroxyethoxymethyl)purine

Product 1

HCID 205176752-Amino-9-(2-hydroxyethoxymethyl)adenine hydrochlorideYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-9-(2-hydroxyethoxymethyl)adenine (0.25 g) was dissolved in hot ethanol (50 ml) and the solution cooled in an ice bath. To the cool solution was added sufficient HCl-saturated ethanol to give a pH of 1.0. Dry ether (50 ml) was then added and the mixture thoroughly chilled. The resulting flesh-colored solid was removed by filtration and washed with cold ethanol. Recrystallization from methanol yielded 2-amino-9-(2-hydroxyethoxymethyl)adenine hydrochloride (0.21 g., 74% of theoretical), m.p. 207°-211° C. Elemental analysis and NMR support this structure.

Workup

  1. temperaturethe solution cooled in an ice bath
  2. customto give a pH of 1.0
  3. temperaturethe mixture thoroughly chilled
  4. customThe resulting flesh-colored solid was removed by filtration
  5. washwashed with cold ethanol
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-07080f2585534544a2ac55064b59ed2e
Source dataset
uspto-grants-1982_04
Patent number
US04323573

Reaction notes

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