5-(2-Methylsulfonylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one → (s)-5-[2-(1-Phenylethylamino)pyrimidin-4-yl]-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

HRID 394476Notes

Reaction equation

HRID 394476 reaction equation
CS([C:5]1[N:10]=[C:9]([CH:11]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)=[N:15][NH:14][C:13](=[O:27])[CH2:12]2)[CH:8]=[CH:7][N:6]=1)(=O)=O>O1CCCC1>[C:17]1([CH:16]([NH:15][C:5]2[N:10]=[C:9]([C@H:11]3[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:24])([F:26])[F:25])[CH:18]=4)=[N:15][NH:14][C:13](=[O:27])[CH2:12]3)[CH:8]=[CH:7][N:6]=2)[CH3:11])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 181766135-(2-Methylsulfonylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 70023896(s)-5-[2-(1-Phenylethylamino)pyrimidin-4-yl]-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 7 (5.00 g, 13.1 mmol), s-(−)-α-methylbenzylamine (3.37 mL, 26.2 mmol) and tetrahydrofuran (100 mL) were heated to reflux under argon for 24 h. The solvent was removed in vacuo. Purification by flash column chromatography (methylene chloride:methanol: ammonium hydroxide 98:2:0.2) gave Compound 8 as a foam: 5.0 g (9.6 mmol, 73%).

Workup

  1. temperatureto reflux under argon for 24 h
  2. customThe solvent was removed in vacuo
  3. customPurification by flash column chromatography (methylene chloride:methanol: ammonium hydroxide 98:2:0.2)

Sources & evidence

ORD record
ord-92c6149c9f0046d296c6220e1fc99766
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Reaction notes

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