Sodium Hydroxide → 2-(2-(Cyclohexyl(methyl)amino)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoic acid

HRID 1399583Notes

Reaction equation

HRID 1399583 reaction equation
[CH:1]1([N:7]([CH3:30])[C:8]2[N:13]=[C:12]([CH3:14])[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18]C)=[O:17])=[C:10]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([N:7]([CH3:30])[C:8]2[N:13]=[C:12]([CH3:14])[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([OH:18])=[O:17])=[C:10]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)[N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50997699Methyl 2-(2-(cyclohexyl(methyl)amino)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Product 1

HCID 509976982-(2-(Cyclohexyl(methyl)amino)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 2-(2-(cyclohexyl(methyl)amino)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (61 mg; 0.15 mmol) in methanol (1.5 mL) was added a 10 N sodium hydroxide solution (149 μL; 1.489 mmol) and the mixture was heated at 100° C. for 18 h. 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. The compound was precipitated from a mixture of ethyl acetate and heptane and the formed solid was triturated with heptane to give 40 mg (68%) of the title compound as a white solid. ESI/APCI(+): 396 (M+H). ESI/APCI(−): 350 (M−CO2H); 394 (M−H).

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
  7. customThe compound was precipitated from a mixture of ethyl acetate and heptane
  8. customthe formed solid was triturated with heptane

Sources & evidence

ORD record
ord-51a2b088e1fb42a7940b9ac757eee2a7
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

Loading…