2-Chloropyrimidine → HCID 22873067, compound

HRID 277718Notes

Reaction equation

HRID 277718 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][C@H:9]1[CH2:14][NH:13][CH2:12][C@@H:11]([CH3:15])[NH:10]1>C1(C)C=CC=CC=1>[CH3:8][C@H:9]1[CH2:14][NH:13][CH2:12][C@@H:11]([CH3:15])[N:10]1[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 744042-ChloropyrimidineHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 22873067HCID 22873067, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 820 mg 2-chloropyrimidine and 1.6 g cis-2,6-dimethylpiperazine in 25 mL toluene was heated at reflux temperature for 12 hours. The solvent was evaporated, the residue was basified with 5% sodium hydroxide and extracted with 2×100 mL of dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated to give cis-2,6-dimethyl-1-(2-pyrimidyl)-piperazine. This amine was then used to prepare 2-phenyl-4(5)-[(4-(2-pyrimidinyl)-cis-2,6-dimethylpiperazin-1-yl)-methyl]-imidazole (Compound 140), m.p. 130-135° C., according to the procedures described in Example VIII.

Workup

  1. temperatureat reflux temperature for 12 hours
  2. customThe solvent was evaporated
  3. extractionextracted with 2×100 mL of dichloromethane
  4. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0326e89f9a3d4a01ad48327cecfbd06b
Source dataset
uspto-grants-2002_03
Patent number
US06358955B1

Reaction notes

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