Sodium Acetate → 3-(5-Chloropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 865806Notes

Reaction equation

HRID 865806 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([CH:9]([CH3:26])[C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])([OH:17])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)[N:5]=[CH:4][N:3]=1.C([O-])(=O)C.[Na+]>C(O)C.[Pd]>[Cl:8][C:7]1[C:6]([CH:9]([CH3:26])[C:10]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])([OH:17])[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[N:5][CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 152306333-(4,5-dichloropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Product 1

HCID 152306323-(5-Chloropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-(4,5-dichloropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, enantiomeric pair B (see Preparation 6(iii)) (0.58 g, 1.46 mmol) in ethanol (20 ml) was hydrogenated at atmospheric pressure and at room temperature in the presence of 10% palladium-on-charcoal (45 mg) and sodium acetate (122 mg, 1.5 mmol) for 7 hours. The catalyst was then removed by filtration and the filtrate was concentrated under reduced pressure. "Flash " chromatography of the residue on silica using ethyl acetate as the eluant provided, after combination and evaporation of the appropriate fractions, the title compound (0.35 g, 72%), m.p. 128° C. Found: C,51.68; H,3.89; N,18.58; C16H14ClF2N5O.0.3 H2O requires: C,51.76; H,3.94; N,18.87%.

Workup

  1. customThe catalyst was then removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customprovided
  4. customafter combination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-9d58a9d12dc54b1ca85c622fbe01be29
Source dataset
uspto-grants-1996_10
Patent number
US05567817

Reaction notes

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