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

HRID 440241Notes

Reaction equation

HRID 440241 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-f3d81110560c4928ad31f4577e9f645f
Source dataset
uspto-grants-1996_05
Patent number
US05519016

Reaction notes

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