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

HRID 1197849Notes

Reaction equation

HRID 1197849 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.0.03 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-f1234b9c95da41f9bd2faff813f53201
Source dataset
uspto-grants-1994_01
Patent number
US05278175

Reaction notes

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