Water → Aditeren

HRID 462526

Reaction equation

HRID 462526 reaction equation
O.[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([NH2:19])=[C:13]([O:20][CH3:21])[CH:12]=2)=[C:5](Cl)[N:4]=1>[Hg](Cl)Cl.[Zn].C(O)(=O)C>[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([CH2:10][C:11]2[CH:12]=[C:13]([O:20][CH3:21])[C:14]([NH2:19])=[C:15]([O:17][CH3:18])[CH:16]=2)=[CH:5][N:4]=1

Participants

6

Reactant 2

HCID 962WaterHCID 212809932,4-Diamino-5-(4-amino-3,5-dimethoxy-benzyl)-6-chloropyrimidine

Product 1

HCID 176875Aditeren

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 0.1 g. of mercury (II) chloride in 2 ml. of water and 1.5 g. of zinc powder was added to a solution of 1.5 g. of 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-6-chloropyrimidine in 15.5 ml. of glacial acetic acid and the mixture was boiled under reflux with stirring overnight. Then, the mixture was filtered while hot and the zinc powder washed with 5 ml. of acetic acid. The combined filtrates were added dropwise with stirring at a temperature below 20° C. to 40 ml. of concentrated ammonia. Then, the mixture was stirred at 20° C. for an additional hour and the solid material was removed by filtration under vacuum, washed with water, dried, recrystallized from methanol and there was obtained 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-pyrimidine having a melting point of 214° C.

Workup

  1. temperatureunder reflux
  2. filtrationThen, the mixture was filtered while hot and the zinc powder
  3. washwashed with 5 ml
  4. additionThe combined filtrates were added dropwise
  5. stirringwith stirring at a temperature below 20° C. to 40 ml
  6. stirringThen, the mixture was stirred at 20° C. for an additional hour
  7. customthe solid material was removed by filtration under vacuum
  8. washwashed with water
  9. customdried
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-299ac4868f0c4bd7a5ae90f14d411515
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Linked notes

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