(E)-5-(1-(4-fluorophenyl)prop-1-enyl)-2-(piperazin-1-yl)pyrimidine → 5-[1-(4-Fluorophenyl)propyl]-2-(1-piperazinyl)pyrimidine

HRID 1498847Notes

Reaction equation

HRID 1498847 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:11]2[CH:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:15][CH:16]=2)=[CH:9]\[CH3:10])=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11]2[CH:12]=[N:13][C:14]([N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[N:15][CH:16]=2)[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 118023005(E)-5-(1-(4-fluorophenyl)prop-1-enyl)-2-(piperazin-1-yl)pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 1180223335-[1-(4-Fluorophenyl)propyl]-2-(1-piperazinyl)pyrimidineYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-5-(1-(4-fluorophenyl)prop-1-enyl)-2-(piperazin-1-yl)pyrimidine (170 mg, 0.57 mmol) in methanol (10 mL) was added Pd/C (30 mg). The mixture was exposed to 1 atm hydrogen (balloon) and stirred at RT for 1 h. The mixture was filtrated, and the filtrate was concentrated to an oil, which was purified by combiflash with dichloromethane:methanol=50:1 to give the title compound (racemate, 90 mg, 53%) as a yellow oil.

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationthe filtrate was concentrated to an oil, which
  3. customwas purified by combiflash with dichloromethane

Sources & evidence

ORD record
ord-90f850df2b014523b0b510ec637304ad
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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