Sodium Dithionite → 2,5,6-Triamino-4-Benzyloxypyrimidine

HRID 260148Notes

Reaction equation

HRID 260148 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N:9]([C:11]1[C:12]([NH2:26])=[N:13][C:14]([NH2:25])=[N:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O>O>[NH2:25][C:14]1[N:13]=[C:12]([NH2:26])[C:11]([NH2:9])=[C:16]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:15]=1

Participants

4

Reactant 2

HCID 24489Sodium DithioniteHCID 1810292,4-Pyrimidinediamine, 5-nitroso-6-(phenylmethoxy)-

Product 1

HCID 98160442,5,6-Triamino-4-Benzyloxypyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium dithionite is added in portions to a suspension of 17 g 5-nitroso-2,4-diamino-6-benzyloxy-primidine (8) in 300 mL H2O at 50° C. until the red nitroso compound is fully reduced. The free base is separated out by adding aqueous ammonia. The crude product is cooled, suctioned off and crystallized from water, to which activated charcoal and a trace of sodium dithionite is added yielding 9.

Workup

  1. customThe free base is separated out
  2. additionby adding aqueous ammonia
  3. temperatureThe crude product is cooled
  4. customcrystallized from water, to which activated charcoal
  5. additiona trace of sodium dithionite is added
  6. customyielding 9

Sources & evidence

ORD record
ord-6eaf1c356d9a405986b556361f156d09
Source dataset
uspto-grants-1996_06
Patent number
US05525711

Reaction notes

Loading…