Hydrochloric Acid → 2,6-Diaminopurine

HRID 1018117Notes

Reaction equation

HRID 1018117 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([N:11]=[N+]=[N-])[N:3]=1.Cl>CO.[Pd]>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 197576806-Azido-7H-purin-2-amine

Product 1

HCID 309762,6-DiaminopurineYield 46.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

9-(R) -2-phosphonomethoxypropyl) -2-amino-6-azidopurine (0.30 g, prepared according to Example 27) in 50% aqueous methanol (200 ml) containing hydrochloric acid (0.5 ml) was hydrogenated over 10% Pd/C (0.5 g) overnight at room temperature. The mixture was filtered, washed with water, filtrate alkalized with ammonia and evaporated in vacuo. The residue was deionized on a column of Dowex 50×8 (50 ml) (cf. Example 25) and the ammonia eluate evaporated to dryness. The residue in water (pH adjusted to 9) was applied on a column of Dowex 1×2 (acetate) which was first washed with water to remove salts and the product was then eluted with 1 M acetic acid. The fractions containing product were pooled, evaporated to dryness and codistilled with water (3×20 ml). The residue was crystallized from water (ethanol added to turbidity) to afford 9-(R)-2-phosphonomethoxypropyl)-2,6-diaminopurine (120 mg) identical with the preparation according to Example 19.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with water, filtrate
  3. customevaporated in vacuo
  4. customthe ammonia eluate evaporated to dryness
  5. washwas first washed with water
  6. customto remove salts
  7. washthe product was then eluted with 1 M acetic acid
  8. additionThe fractions containing product
  9. customevaporated to dryness
  10. customThe residue was crystallized from water (ethanol added to turbidity)

Sources & evidence

ORD record
ord-132b52552a9c4776aaf452965ceffa6d
Source dataset
uspto-grants-2002_11
Patent number
US06479673B1

Reaction notes

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