5-Isopropenyl-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidine → 5-Isopropyl-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidine

HRID 42165Notes

Reaction equation

HRID 42165 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][O:23][C:24]4[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=4)=[N:20][CH:21]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([CH3:3])=[CH2:2]>CO.[C].[Pd]>[CH:1]([C:4]1[CH:5]=[N:6][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:17]=[CH:18][C:19]([CH2:22][O:23][C:24]4[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:31])=[O:32])=[CH:28][CH:29]=4)=[N:20][CH:21]=3)[CH2:12][CH2:11]2)=[N:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 670832375-Isopropenyl-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidine

Product 1

HCID 670830295-Isopropyl-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidineYield 71.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-isopropenyl-2-[4-[2-(4-methanesulfonylphenoxymethyl)pyridin-5-yl]piperidin-1-yl]pyrimidine (Example 58) (21 mg, 0.045 mmol) in methanol (0.45 mL) was added 10% palladium-carbon (10 mg). The mixture was hydrogenated at room temperature for 1 hour and filtered through Celite pad. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the title compound as a white crystal (15 mg, yield 71%).

Workup

  1. filtrationfiltered through Celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-3559dbb87a5e42068d107d1e4d553271
Source dataset
uspto-grants-2013_09
Patent number
US08536176B2

Reaction notes

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