Sodium Hydroxide → HCID 50996618, compound

HRID 1399602Notes

Reaction equation

HRID 1399602 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:14]=[C:13]([CH3:15])[C:12]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19]C)=[O:18])=[C:11]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[N:10]=2)[CH2:3]1.[OH-].[Na+]>CO>[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:14]=[C:13]([CH3:15])[C:12]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([OH:19])=[O:18])=[C:11]([C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[N:10]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50996444HCID 50996444, compound

Product 1

HCID 50996618HCID 50996618, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(2-(3,5-dimethylpiperidin-1-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.090 g; 0.227 mmol) in methanol (3 mL) was added a solution of sodium hydroxide 5N (0.488 mL; 2.44 mmol) and the reaction mixture was heated to reflux for 18 h. The volatiles were removed under reduced pressure, the residue was dissolved in water and the pH of the solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N. The formed precipitate was collected by filtration and dried under reduced pressure over P2O5 to give 0.067 g (69%) of the title compound as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue was dissolved in water
  5. additionthe pH of the solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N
  6. filtrationThe formed precipitate was collected by filtration
  7. dry with materialdried under reduced pressure over P2O5

Sources & evidence

ORD record
ord-5e25e00cc9a34e7382201be394d9b0dd
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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