HCID 18444274, compound → HCID 18444284, compound

HRID 459869Notes

Reaction equation

HRID 459869 reaction equation
O.Cl[C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=4)[N:18]=3)=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][N:4]=1>[Pd].CO>[CH3:32][O:31][C:25]1[CH:24]=[C:23]([C:19]2[N:18]=[C:17]([C:15]([N:12]3[CH2:13][CH2:14][N:9]([C:7]4[CH:6]=[CH:5][N:4]=[CH:3][N:8]=4)[CH2:10][CH2:11]3)=[O:16])[CH:22]=[CH:21][CH:20]=2)[CH:28]=[CH:27][C:26]=1[O:29][CH3:30]

Participants

4

Reactant 1

HCID 18444274HCID 18444274, compound

Product 1

HCID 18444284HCID 18444284, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a methanol (20 ml) solution of 460 mg of 2-chloro-4-{4-[6-(3,4-dimethoxyphenyl) pyridine-2-carbonyl]piperazin-1-yl}pyrimidine monohydrate was added 150 mg of 10% palladium/carbon, followed by 23 hours of stirring at room temperature under a hydrogen atmosphere of normal pressure. Insoluble matter was removed by filtration and the residue obtained by evaporation of the solvent was purified by silica gel column chromatography (chloroform-methanol) and further, recrystallization was carried out from acetonitrile-diisopropyl ether to obtain 83 mg of 4-{4-[6-(3,4-dimethoxyphenyl)pyridine-2-carbonyl]piperazin-1-yl}pyrimidine as colorless crystals.

Workup

  1. customInsoluble matter was removed by filtration
  2. customthe residue obtained by evaporation of the solvent
  3. customwas purified by silica gel column chromatography (chloroform-methanol)
  4. customfurther, recrystallization

Sources & evidence

ORD record
ord-27ea30648b7e4d368ee7ee478583cdcd
Source dataset
uspto-grants-2007_03
Patent number
US07196080B2

Reaction notes

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