Sodium Hydroxide → 2-(4-Methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoic acid

HRID 1399600Notes

Reaction equation

HRID 1399600 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11]C)=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[N:5]=[C:4]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)[N:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)[N:5]=[C:4]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50996969Methyl 2-(4-methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 498708932-(4-Methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoic acidYield 107.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(4-methyl-2-(4-methylpiperazin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate (0.042 g; 0.105 mmol) in methanol (2 mL) was added a solution of sodium hydroxide 5N (0.131 mL; 0.656 mmol) and the reaction mixture was heated to reflux for 48 h. The volatiles were removed under reduced pressure, the residue dissolved in water and the pH was adjusted to 5 by addition of a solution of hydrochloric acid 2N. The formed precipitate was collected by filtration and dried under reduced pressure. Purification by preparative HPLC (HPLC method 4) furnished 0.043 g (58%) of the title compound as a solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 48 h
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue dissolved in water
  5. additionthe pH was adjusted to 5 by addition of a solution of hydrochloric acid 2N
  6. filtrationThe formed precipitate was collected by filtration
  7. customdried under reduced pressure
  8. customPurification by preparative HPLC (HPLC method 4)

Sources & evidence

ORD record
ord-fb0f2e47d9424f4285090f712c00b472
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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