4-(4-Benzyl-phthalazin-1-yl)-5'-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl → 4-(4-Benzyl-phthalazin-1-yl)-5'-isopropyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 42195Notes

Reaction equation

HRID 42195 reaction equation
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[N:28][C:27]([C:30]([CH3:32])=[CH2:31])=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[CH:29]=[N:28][C:27]([CH:30]([CH3:32])[CH3:31])=[CH:26][N:25]=3)[CH2:22][CH2:23]2)=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 592405284-(4-Benzyl-phthalazin-1-yl)-5'-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinylHCID 178418361HCID 178418361, compound

Product 1

HCID 592405794-(4-Benzyl-phthalazin-1-yl)-5'-isopropyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinylYield 35.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

4-(4-Benzyl-phthalazin-1-yl)-5′-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (50 mg, 0.118 mmol) is dissolved in MeOH (2 mL). Palladium hydroxide (25 mg) is added to the flask capped with a septum and balloon of hydrogen. The reaction is stirred 3 h at room temperature. Filter through a small pad of silica gel and wash behind with EtOAc. Concentrate the filtrate in vacuo. The residue is purified by flash chromatography on silica gel (EtOAc/Heptane) to afford the title compound (17.6 mg, 35%).

Workup

  1. filtrationFilter through a small pad of silica gel
  2. washwash behind with EtOAc
  3. concentrationConcentrate the filtrate in vacuo
  4. customThe residue is purified by flash chromatography on silica gel (EtOAc/Heptane)

Sources & evidence

ORD record
ord-d74706ed3ac24d79bb04930829d83091
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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