Hydrazine → 4-(4-Chlorophenyl)-6-hydrazinylpyrimidine

HRID 271406Notes

Reaction equation

HRID 271406 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[NH2:15][NH2:16]>C1COCC1>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:7]=[C:2]([NH:15][NH2:16])[N:3]=[CH:4][N:5]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 249020894-Chloro-6-(4-chlorophenyl)pyrimidine

Product 1

HCID 587728354-(4-Chlorophenyl)-6-hydrazinylpyrimidineYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 4-chloro-6-(4-chlorophenyl)pyrimidine (1.25 g, 5.6 mmol) in THF (10 mL) at room temperature under argon was added H2NNH2 (538 mg, 16.8 mmol). The reaction mixture was heated at 60° C. under argon for 2 h. Analysis by HPLC/MS indicated that the reaction was complete. About three fourths of the solvent was evaporated and Et2O (5 mL) was added to the resulting suspension. After stirring at room temperature for 20 min, solid was collected by filtration and further washed with Et2O (15 mL), then dried under vacuum to obtain 831 mg of the title compound as a white solid. HPLC/MS: retention time=1.88 min, [M+H]30 =221.

Workup

  1. customAbout three fourths of the solvent was evaporated
  2. additionEt2O (5 mL) was added to the resulting suspension
  3. filtrationsolid was collected by filtration
  4. washfurther washed with Et2O (15 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-af32e46d1ffd43f9b6bde54a73e0ae39
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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