Sodium Hydroxide → 4,4-Dimethyl-2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoic acid

HRID 1399722Notes

Reaction equation

HRID 1399722 reaction equation
[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][CH:4]([C:9]1[C:10]([CH3:28])=[N:11][C:12]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO>[CH3:1][C:2]([CH3:30])([CH3:29])[CH2:3][CH:4]([C:9]1[C:10]([CH3:28])=[N:11][C:12]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50994998Methyl 4,4-dimethyl-2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 509973204,4-Dimethyl-2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoic acidYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared according to general method D from methyl 4,4-dimethyl-2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate (0.024 g; 0.059 mmol), sodium hydroxide 10N (0.100 mL; 1.00 mmol) in methanol (1 mL) at 60° C. for 18 h. Purification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane, followed by a purification by preparative HPLC (HPLC method 1) furnished 0.007 g (29%) of the title compound as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-e8cc159623ac42839e05b93097b2adfc
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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