Methane → 6-[3-amino-4-[4-(2-pyrimidyl)-piperazin-1-yl]phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

HRID 1031476Notes

Reaction equation

HRID 1031476 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:22]2[CH:23]([CH3:29])[CH2:24][C:25](=[O:28])[NH:26][N:27]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:12][CH2:11]1)([O-])=O.C>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:22]2[CH:23]([CH3:29])[CH2:24][C:25](=[O:28])[NH:26][N:27]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:17]=[CH:18][CH:19]=[CH:20][N:21]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 297MethaneHCID 144594656-[3-nitro-4-[4-(2-pyrimidyl)-piperazin-1-yl]phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone

Product 1

HCID 144595026-[3-amino-4-[4-(2-pyrimidyl)-piperazin-1-yl]phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinoneYield 30.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.5 g (6.3 mmol) of 6-[3-nitro-4[4-(2-pyrimidyl)-piperazin-1-yl]-phenyl]-4,5-dihydro-5-methyl-3(2H)-pyridazinone in 130 ml of methanol are hydrogenated under a hydrogen pressure of 5 bar in the presence of 0.3 g of palladium on active charcoal (10% Pd) at 50° C. for 3 hours. After removal of the catalyst by suction filtration, the filtrate is highly concentrated by evaporation under vacuum and the residue obtained is chromatographed on silica gel, using dichloromethane/methanol (95:5) as solvent. After concentration of the product fractions by evaporation, the residue obtained is crystallized with acetone. 0.70 g (30%) of pale beige crystals, m.p. 220° to 221° C., are obtained.

Workup

  1. customat 50° C.
  2. customfor 3 hours
  3. customAfter removal of the catalyst
  4. filtrationby suction filtration
  5. concentrationthe filtrate is highly concentrated by evaporation under vacuum
  6. customthe residue obtained
  7. customis chromatographed on silica gel
  8. customAfter concentration of the product fractions by evaporation
  9. customthe residue obtained
  10. customis crystallized with acetone

Sources & evidence

ORD record
ord-21d49d072f044432a5efbcc5d5ff3a8c
Source dataset
uspto-grants-1990_09
Patent number
US04954501

Reaction notes

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