2-(5-Nitro-2-propoxyphenyl)-8-azapurin-6-one → 2-(5-Amino-2-propoxyphenyl)-8-azapurin-6-one

HRID 1863136Notes

Reaction equation

HRID 1863136 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][CH2:22][CH3:23])=[C:8]([C:10]2[N:18]=[C:17]3[C:13](=[N:14][N:15]=[N:16]3)[C:12](=[O:19])[N:11]=2)[CH:9]=1)([O-])=O>C(OCCO)C.[Pt]=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:20][CH2:21][CH2:22][CH3:23])=[C:8]([C:10]2[N:18]=[C:17]3[C:13](=[N:14][N:15]=[N:16]3)[C:12](=[O:19])[N:11]=2)[CH:9]=1

Participants

4

Reactant 1

HCID 203929622-(5-Nitro-2-propoxyphenyl)-8-azapurin-6-one

Product 1

HCID 203929612-(5-Amino-2-propoxyphenyl)-8-azapurin-6-oneYield 41.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8076Glycol monoethyl etherSolvent

Procedure

2-(5-Nitro-2-propoxyphenyl)-8-azapurin-6-one (32 g) was dissolved in 2-ethoxyethanol (400 ml) and the solution was hydrogenated under a hydrogen pressure of 5 kg/cm2 at 30° C. using platinum oxide (3 g) as catalyst. After 3 hours when reaction was complete, the catalyst was filtered off and the solvent was removed from the filtrate in vacuo. The resulting brown oil was heated at reflux with hydrochloric acid (600 ml; 2 N) and the mixture was then treated with charcoal and filtered. The filtrate was cooled and treated with concentrated aqueous ammonia solution until alkaline, and then was again treated with charcoal and filtered. The filtrate was acidified to pH 4 by treatment with glacial acetic acid and left to stand at 0° C. for 24 hours. The resulting yellow solid was filtered off and recrystallised from ethanol to give 2-(5-amino-2-propoxyphenyl)-8-azapurin-6-one (12.0 g), m.p. 225°-227° C.

Workup

  1. customat 30° C.
  2. customAfter 3 hours when reaction
  3. filtrationthe catalyst was filtered off
  4. customthe solvent was removed from the filtrate in vacuo
  5. temperatureThe resulting brown oil was heated
  6. temperatureat reflux with hydrochloric acid (600 ml; 2 N)
  7. additionthe mixture was then treated with charcoal
  8. filtrationfiltered
  9. temperatureThe filtrate was cooled
  10. additiontreated with concentrated aqueous ammonia solution until alkaline
  11. additionwas again treated with charcoal
  12. filtrationfiltered
  13. waitleft
  14. filtrationThe resulting yellow solid was filtered off
  15. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-9129bf932b4a4b7ab85cb241a9782e6d
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

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