2-Chloro-4,6-dimethylpyrimidine → HCID 36550877, compound

HRID 1910808Notes

Reaction equation

HRID 1910808 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:17]1[N:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=1>N1C=CC=CC=1>[CH3:24][C:19]1[CH:20]=[C:21]([CH3:23])[N:22]=[C:17]([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[N:18]=1

Participants

4

Reactant 2

HCID 205502-Chloro-4,6-dimethylpyrimidineHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 36550877HCID 36550877, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-(4-Nitrophenyl)-piperazine (2.18 g, 10.6 mmol) was added to 2-chloro-4,6-dimethyl-pyrimidine (1.5 g, 10.6 mmol) in pyridine (10 mL) and the mixture was heated at reflux for 7 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was separated, washed with water and brine, dried over anhydrous sodium sulfate and concentrated to afford 4,6-dimethyl-2-[4-(4-nitro-phenyl)-piperazin-1-yl]-pyrimidine (0.8 g, 24%) as a solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 7 h
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between ethyl acetate and water
  5. customThe organic phase was separated
  6. washwashed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-53f9af4588ed40d28a830f581beaee68
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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