Sodium Hydroxide → 2-[4-(2-Chloro-4-methyl-phenyl)-6-methyl-2-(1-piperidyl)pyrimidin-5-yl]pentanoic acid

HRID 1399714Notes

Reaction equation

HRID 1399714 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18]C)=[O:17])=[C:13]([CH3:23])[N:12]=[C:11]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[N:10]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([OH:18])=[O:17])=[C:13]([CH3:23])[N:12]=[C:11]([N:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[N:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66955346Methyl 2-(4-(2-chloro-4-methylphenyl)-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate

Product 1

HCID 669563692-[4-(2-Chloro-4-methyl-phenyl)-6-methyl-2-(1-piperidyl)pyrimidin-5-yl]pentanoic acidYield 49.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared according to general method D from methyl 2-(4-(2-chloro-4-methylphenyl)-6-methyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.069 g; 0.166 mmol), sodium hydroxide 10N (0.200 mL; 2.00 mmol) in methanol (2 mL) at 60° C. for 18 h. Purification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane furnished 0.033 g (44%) of the title compound as a white solid.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane

Sources & evidence

ORD record
ord-3266758c0e35465ca044dbffb5bb6b04
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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