Ammonia → 2,6-Diamino-9-(2-hydroxyethoxymethyl)purine

HRID 614930Notes

Reaction equation

HRID 614930 reaction equation
Cl[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.[NH3:17]>>[NH2:17][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

3

Reactant 2

HCID 222AmmoniaHCID 128995862-Chloro-9-(2-hydroxyethoxymethyl)adenine

Product 1

HCID 945882,6-Diamino-9-(2-hydroxyethoxymethyl)purineYield 12%

Conditions

Temperature
120 °C

Procedure

A mixture of 2-chloro-9-(2-hydroxyethoxymethyl)adenine (4.4g) and liquid ammonia (40ml) was heated at 120° C. in a bomb for 19 hours. The reaction mixture was removed from the bomb and excess ammonia removed in vacuo. The residue was partitioned between ether and water and the aqueous layer washed twice more with ether and once with chloroform. The aqueous solution was then treated with an excess of a strongly basic ion exchange resin to convert the ammonium chloride to ammonia and evaporated to dryness in vacuo. The residue was dissolved in a minimal amount of ethanol, Florisil (Registered Trade Mark) (10g) added, and the mixture evaporated in dryness. The residue was transferred to a prepared column of Florisil in chloroform and eluted with 5% methanol/95% chloroform (v/v). Fractions (30ml) were collected and examined by TLC (silica gel plates developed in 10% methanol/90% chloroform) for the presence of product. The first 40 fractions contained starting material but no product and were discarded. Succeeding fractions which were found to contain the desired product were combined and evaporated to dryness. The residue was recrystallized from ethanol (with activated charcoal treatment) and from n-propanol to give 2-amino-9-(2-hydroxyethoxymethyl)adenine (0.5g, 12% of theoretical), m.p. 183°-184° C.

Workup

  1. customThe reaction mixture was removed from the bomb and excess ammonia
  2. customremoved in vacuo
  3. customThe residue was partitioned between ether and water
  4. washthe aqueous layer washed twice more with ether and once with chloroform
  5. additionThe aqueous solution was then treated with an excess of a strongly basic ion exchange resin
  6. customevaporated to dryness in vacuo
  7. dissolutionThe residue was dissolved in a minimal amount of ethanol, Florisil (Registered Trade Mark) (10g)
  8. additionadded
  9. customthe mixture evaporated in dryness
  10. washeluted with 5% methanol/95% chloroform (v/v)
  11. customFractions (30ml) were collected
  12. customevaporated to dryness
  13. customThe residue was recrystallized from ethanol (with activated charcoal treatment) and from n-propanol

Sources & evidence

ORD record
ord-bc4a109344f241678973c50ca6c86856
Source dataset
uspto-grants-1979_03
Patent number
US04146715

Reaction notes

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