1-Methylpiperazine → HCID 178480770, compound

HRID 1591579

Reaction equation

HRID 1591579 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[N:11]=[C:10]([OH:20])[CH:9]=2)[CH:3]=1.[CH3:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CC(O)(CC)C.[Cl-].[Zn+2].[Cl-]>[CH3:21][N:22]1[CH2:27][CH2:26][N:25]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]3[N:13]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=4)[N:11]=[C:10]([OH:20])[CH:9]=3)[CH:3]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 1785156306-(4-chloro-2-pyridinyl)-2-pyridin-2-yl-1H-pyrimidin-4-one

Product 1

HCID 178480770HCID 178480770, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of 3.51 g (12.3 mmol) of 6-(4-chloropyrid-2-yl)-2-pyrid-2-yl-pyrimidin-4-ol, 27.4 ml (303 mmol, 20 equivalents, 30.38 g) of 1-methyl-piperazine and 84 mg (0.05 mmol, 0.05 equivalent) of zinc(II) chloride in 50 ml of 2-methyl-2-butanol is refluxed for 22 hours and concentrated to dryness using a rotary evaporator. 50 ml of water are added, 3.6 g of EDTA are added, and the pH is adjusted to 9 using dilute sodium hydroxide solution. Extraction is carried out three times using 150 ml of chloroform each time, and the organic extracts are combined and dried (sodium sulfate). Concentration is carried out using a rotary evaporator and the crude product is recrystallised from toluene. 6-[4-(4-Methyl-piperazin-1-yl)-pyrid-2-yl]-2-pyrid-2-yl-pyrimidin-4-ol is obtained in the form of a whitish solid.

Workup

  1. temperatureis refluxed for 22 hours
  2. concentrationconcentrated to dryness
  3. customa rotary evaporator
  4. addition50 ml of water are added
  5. addition3.6 g of EDTA are added
  6. extractionExtraction
  7. dry with materialdried (sodium sulfate)
  8. concentrationConcentration
  9. customa rotary evaporator
  10. customthe crude product is recrystallised from toluene

Sources & evidence

ORD record
ord-39eba654b162417ca0638b4a13f20a5a
Source dataset
uspto-grants-2007_11
Patent number
US07291584B2

Linked notes

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