1-(4-Trifluoromethyl-6-chloropyrimidin-5-yl)-1-(2-chloro-4-methoxypyrimidin-5-yl)methanol → 1-(4-Trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)methanol

HRID 861391Notes

Reaction equation

HRID 861391 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[C:8]([CH:9]([C:11]2[C:12]([O:18][CH3:19])=[N:13][C:14](Cl)=[N:15][CH:16]=2)[OH:10])=[C:7](Cl)[N:6]=[CH:5][N:4]=1>[Pd]>[F:22][C:2]([F:1])([F:21])[C:3]1[C:8]([CH:9]([C:11]2[C:12]([O:18][CH3:19])=[N:13][CH:14]=[N:15][CH:16]=2)[OH:10])=[CH:7][N:6]=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 197027971-(4-Trifluoromethyl-6-chloropyrimidin-5-yl)-1-(2-chloro-4-methoxypyrimidin-5-yl)methanol

Product 1

HCID 197028001-(4-Trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

1-(4-trifluoromethyl-6-chloropyrimidin-5-yl)-1-(2-chloro-4-methoxypyrimidin-5-yl)methanol (0.21 g, 0.59 mmol) was stirred under a hydrogen atmosphere at room temperature with MgO (142 mg, 3.35 mmol, 6 equivalents), and 10% palladium on carbon (Pd/C) (25 mg, Degussa, 50% wet by weight). After 3 hours, an additional 30 mg of 10% Pd/C was added and the solution stirred for 4 hours, filtered over celite and concentrated in vacuo. Preparative radial chromatography (SiO2 ; hexane/EtOAc gradient elution) afforded the desired product, 81 mg (48%) as an oil.

Workup

  1. filtrationfiltered over celite and
  2. concentrationconcentrated in vacuo
  3. washPreparative radial chromatography (SiO2 ; hexane/EtOAc gradient elution)

Sources & evidence

ORD record
ord-0928b632cf984725acce8b47c913218f
Source dataset
uspto-grants-1998_02
Patent number
US05714438

Reaction notes

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