Sodium Hydroxide → 2-(4-Methyl-2,6-dip-tolylpyrimidin-5-yl)pentanoic acid

HRID 1399581Notes

Reaction equation

HRID 1399581 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]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH: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]([C:23]2[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66955816Methyl 2-(4-methyl-2,6-dip-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 669559252-(4-Methyl-2,6-dip-tolylpyrimidin-5-yl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-(4-methyl-2,6-dip-tolylpyrimidin-5-yl)pentanoate (86 mg; 0.221 mmol) in methanol (2.214 ml) was added a 10 N sodium hydroxide solution (221 μl; 2.21 mmol) and the mixture was heated at 100° C. overnight. The volatiles were removed under reduced pressure and the mixture was acidified by adding 6N hydrochloric acid. The suspension was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionby adding 6N hydrochloric acid
  3. extractionThe suspension was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f6131ff8e4cf4dc79d3051a42ce566a2
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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