Sodium Hydroxide → 6-(Cyclohexyloxy)pyrimidine-4-carboxylic acid

HRID 1746673Notes

Reaction equation

HRID 1746673 reaction equation
[CH:1]1([O:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([O:16]C3CCCCC3)=[O:15])[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CCO.O>[CH:1]1([O:7][C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=[O:15])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59446917Cyclohexyl 6-(cyclohexyloxy)pyrimidine-4-carboxylate

Product 1

HCID 594470626-(Cyclohexyloxy)pyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

A solution of cyclohexyl 6-(cyclohexyloxy)pyrimidine-4-carboxylate (2.00 g; 6.57 mmol) in THF/EtOH/H2O (3/2/1, total volume 200 mL) was treated with a 5N solution of sodium hydroxide (3.94 ml; 19.7 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated under vacuum and then water was added. The aqueous layer was washed with DCM then acidified to pH 5 by addition of 1N HCl solution. The aqueous layer was washed with EtOAc (150 mL), then lyophilized and the obtained solid was washed with DCM. The suspension was filtered off and the filtrate was concentrated under vacuum to afford the title compound as a beige solid.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionwater was added
  3. washThe aqueous layer was washed with DCM
  4. additionthen acidified to pH 5 by addition of 1N HCl solution
  5. washThe aqueous layer was washed with EtOAc (150 mL)
  6. washthe obtained solid was washed with DCM
  7. filtrationThe suspension was filtered off
  8. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-aae3ae94e79543998ee99fb745877637
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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