Hydrazine hydrate (1:1) → N-amino-N'-(2-chlorophenyl)pyrimidine-4-carboxamidine

HRID 509582Notes

Reaction equation

HRID 509582 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:23][NH2:24].O>C1(C)C=CC=CC=1>[NH2:23][NH:24][C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)=[N:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 24819Phosphorus pentachlorideHCID 67958692N-(2-chlorophenyl)pyrimidine-4-carboxamide

Product 1

HCID 67958854N-amino-N'-(2-chlorophenyl)pyrimidine-4-carboxamidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of N-(2-chlorophenyl)pyrimidine-4-carboxamide 3 (0.2 g, 0.86 mmol) in 20 mL of PhMe was added 0.65 g of PCl5. The mixture was stirred at reflux for 3 h. To this solution was added 3 mL of NH2NH2.H2O. The mixture was stirred at ambient temperature for 2 h. After removal of all solvent, the residue was purified by column (2:1 of hexane/ethyl acetate) to give N-amino-N′-(2-chlorophenyl)pyrimidine-4-carboxamidine 5 as a solid. Yield: 0.15 g, 70%.

Workup

  1. temperatureat reflux for 3 h
  2. stirringThe mixture was stirred at ambient temperature for 2 h
  3. customAfter removal of all solvent
  4. customthe residue was purified by column (2:1 of hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8925a77f82a849118c6aebc9b8afd4e1
Source dataset
uspto-grants-2015_08
Patent number
US09096587B2

Reaction notes

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