2-Amino-5-nitrobenzonitrile → 2,4,6-Triaminoquinazoline

HRID 2216322Notes

Reaction equation

HRID 2216322 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].[Na].N[C:11]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:12]=1[C:13]#[N:14]>CO>[N:7]1[C:11]2[C:12](=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)[C:13]([NH2:14])=[N:5][C:6]=1[NH2:8]

Participants

5

Reactant 3

HCID 285322-Amino-5-nitrobenzonitrileHCID 286947Carbonic acid-guanidine (1:1)HCID 5360545Sodium

Product 1

HCID 2926612,4,6-Triaminoquinazoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of guanidine carbonate (0.9 g, 5.0 mmol) in 30 mL methanol was added sodium (0.24 g, 10.4 mmol) and the mixture was heated under reflux for 30 minutes. The precipitated sodium carbonate was filtered off and washed with methanol. 2-Amino-5-nitrobenzonitrile (0.88 g, 5.4 mmol) was added to the methanolic solution which was then heated under reflux for additional 24 hours. The solvent was evaporated and the crude 6-nitro-2,4-quinazolinediamine subjected to catalytic hydrogenation as described in EXAMPLE 41.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationThe precipitated sodium carbonate was filtered off
  4. washwashed with methanol
  5. temperaturewas then heated
  6. temperatureunder reflux for additional 24 hours
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-f466e6fa81e7429793916d360aa59407
Source dataset
uspto-grants-2006_09
Patent number
US07112590B2

Reaction notes

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