2-(4-Benzylpiperazin-1-yl)-4,6-dimethoxypyrimidine → 4,6-Dimethoxy-2-(piperazin-1-yl)pyrimidine

HRID 2293986Notes

Reaction equation

HRID 2293986 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([N:11]2[CH2:16][CH2:15][N:14](CC3C=CC=CC=3)[CH2:13][CH2:12]2)[N:4]=1.[H][H]>C(O)C.[C].[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([N:11]2[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]2)[N:4]=1

Participants

5

Reactant 2

HCID 46128712-(4-Benzylpiperazin-1-yl)-4,6-dimethoxypyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 50909284,6-Dimethoxy-2-(piperazin-1-yl)pyrimidineYield 49.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 110 ml of ethanol was dissolved 3.9 g (0.0125 mole) of 4-(4,6-dimethoxy-2-pyrimidinyl)-1-benzylpiperazine obtained as described above, and 2.5 g of 5% palladium carbon was added thereto. While refluxing the mixture under heating, hydrogen gas was passed for 6 hours. The reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of chloroform:methanol=9:1) to obtain 1.38 g of 1-(4,6-dimethoxy-2-pyrimidinyl)piperazine as pale red crystals.

Workup

  1. customobtained
  2. additionwas added
  3. temperatureWhile refluxing the mixture
  4. temperatureunder heating
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. additiona mixture of chloroform

Sources & evidence

ORD record
ord-facb7e3effb84906a3c2f44758e83fd7
Source dataset
uspto-grants-1997_11
Patent number
US05688791

Reaction notes

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