Benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)benzoate → 2-(4,6-Dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)-benzoic acid

HRID 1957093Notes

Reaction equation

HRID 1957093 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[N:29]=3)[C:13]=2[C:14]([O:16]CC2C=CC=CC=2)=[O:15])[N:4]=1.[H][H]>C(OCC)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[N:29]=3)[C:13]=2[C:14]([OH:16])=[O:15])[N:4]=1

Participants

5

Reactant 2

HCID 15279417Benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)benzoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 152794182-(4,6-Dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)-benzoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

1.57 g of benzyl 2-(4,6-dimethoxypyrimidin-2-yloxy)-6-(6-methoxypyridin-2-yl)benzoate and 560 mg of palladium on active carbon (10%) in 100 ml of diethyl ether are hydrogenated at room temperature for 10 h at a hydrogen pressure of 50 bar. A further 300 mg of catalyst are then added and the mixture is hydrogenated at room temperature for another 10 h at a hydrogen pressure of 50 bar. The mixture is filtered through Celite® (Aldrich) and concentrated under reduced pressure. Yield: 0.99 g of a solid of m.p. 158°-160° C.

Workup

  1. filtrationThe mixture is filtered through Celite® (Aldrich)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c2b7c3b1412b43a187fb7e2609dd4fc4
Source dataset
uspto-grants-1998_07
Patent number
US05783521

Reaction notes

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