Carbonic acid-guanidine (1:1) → Aditeren

HRID 462535Notes

Reaction equation

HRID 462535 reaction equation
[Na].C(=O)(O)O.[NH2:6][C:7]([NH2:9])=[NH:8].[NH:10]([CH:17]=[C:18]([C:33]#N)[CH2:19][C:20]1[CH:28]=[C:27]([O:29][CH3:30])[C:23]([NH:24]C=O)=[C:22]([O:31][CH3:32])[CH:21]=1)C1C=CC=CC=1>O>[NH2:8][C:7]1[N:9]=[C:17]([NH2:10])[C:18]([CH2:19][C:20]2[CH:21]=[C:22]([O:31][CH3:32])[C:23]([NH2:24])=[C:27]([O:29][CH3:30])[CH:28]=2)=[CH:33][N:6]=1

Participants

5

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 5360545SodiumHCID 867400924'-(3-Anilino-2-cyano-allyl)-2',6'-dimethoxy-formanilide

Product 1

HCID 176875Aditeren

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.84 g. of sodium in 200 ml. of absolute alcohol was treated with 14.4 g. of guanidine carbonate and 8.9 g. of 4'-(3-anilino-2-cyano-allyl)-2',6'-dimethoxy-formanilide and refluxed for 20 hours. Then, 200 ml. of water were added and the alcohol was removed under vacuum. After standing at room temperature for 2 hours, the crystals formed were removed by filtration with suction, washed with water and recrystallized from methanol, whereby there was obtained 2,4-diamino-5-(4-amino-3,5-dimethoxy-benzyl)-pyrimidine having a melting point of 215°-216° C.

Workup

  1. customthe alcohol was removed under vacuum
  2. customthe crystals formed
  3. customwere removed by filtration with suction
  4. washwashed with water
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-5eb92f88931b43d49b40c670c54eb2a0
Source dataset
uspto-grants-1985_05
Patent number
US04515948

Reaction notes

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