Hydrochloric Acid → 2-(2-Allyloxyphenyl)-8-azapurin-6-one

HRID 1288269Notes

Reaction equation

HRID 1288269 reaction equation
[N:1]([O-])=O.[Na+].Cl.[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[NH:17][C:18](=[O:24])[C:19]([NH2:23])=[C:20]([NH2:22])[N:21]=1)[CH:7]=[CH2:8]>O>[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:21]=[C:20]2[C:19](=[N:23][N:1]=[N:22]2)[C:18](=[O:24])[N:17]=1)[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 1360237872-(2-Allyloxyphenyl)-4,5-diaminopyrimid-6-one

Product 1

HCID 215043612-(2-Allyloxyphenyl)-8-azapurin-6-oneYield 32.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium nitrite (3 g.) was added slowly with stirring to a solution of concentrated hydrochloric acid (100 ml.) in water (100 ml.) maintained at between -5° and 0° C. by means of an ice/salt bath. 2-(2-Allyloxyphenyl)-4,5-diaminopyrimid-6-one (5.1 g.) was then added in portions during 30 minutes with stirring at between -5° and 0° C. The cooling bath was removed, and the mixture stirred at room temperature overnight. The solid which separated was filtered off and dissolved in a solution of concentrated ammonium hydroxide (10 ml.) in water (100 ml.). The solution was heated with charcoal, filtered, and the filtrate acidified with glacial acetic acid. The solid which separated was filtered off and recrystallised from methanol to give 2-(2-allyloxyphenyl)-8-azapurin-6-one (1.7 g.), m.p. 173°-175° C.

Workup

  1. temperaturemaintained at between -5° and 0° C. by means of an ice/salt bath
  2. customThe cooling bath was removed
  3. stirringthe mixture stirred at room temperature overnight
  4. customThe solid which separated
  5. filtrationwas filtered off
  6. dissolutiondissolved in a solution of concentrated ammonium hydroxide (10 ml.) in water (100 ml.)
  7. temperatureThe solution was heated with charcoal
  8. filtrationfiltered
  9. customThe solid which separated
  10. filtrationwas filtered off
  11. customrecrystallised from methanol

Sources & evidence

ORD record
ord-efed079efddf4e43aa38e03fe721aeb7
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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