Sodium Hydroxide → 6-(Cyclohexyloxy)pyrimidine-4-carboxylic acid
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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.