Sodium Hydroxide → HCID 50996968, compound

HRID 1399606Notes

Reaction equation

HRID 1399606 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][CH2:26][CH:25]([CH3:29])[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:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[N:5]=[C:4]([N:23]2[CH2:28][CH2:27][CH2:26][CH:25]([CH3:29])[CH2:24]2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50996791HCID 50996791, compound

Product 1

HCID 50996968HCID 50996968, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(4-methyl-2-(3-methylpiperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate (0.067 g; 0.169 mmol) in methanol (4.1 mL) was added a solution of sodium hydroxide 5% (4.1 mL, 5.12 mmol) and the mixture was stirred at room temperature for 4 days. The volatiles were removed under reduced pressure, the residue dissolved in water and the pH was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N. The formed precipitate was collected by filtration. Purification by preparative HPLC (HPLC method 3) furnished 0.004 g (6%) of the title compound as a solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. additionthe pH was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N
  4. filtrationThe formed precipitate was collected by filtration
  5. customPurification by preparative HPLC (HPLC method 3)

Sources & evidence

ORD record
ord-47bbc518035e467fa8720008404b8200
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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