Lithium Hydroxide → HCID 59446935, compound

Participants

Reaction Steps

A mixture of methyl 2-chloro-6-[(cyclohexylmethyl)amino]pyrimidine-4-carboxylate (Intermediate 3, 2.25 g; 7.93 mmol), palladium on charcoal and triethylamine (3.32 mL; 23.8 mmol) in EtOH (400 mL) was stirred under an atmosphere of hydrogen. After 2 hours the reaction mixture was filtered on celite and evaporated to give a mixture of methyl 6-[(cyclohexylmethyl)amino]pyrimidine-4-carboxylate and ethyl 6-[(cyclohexylmethyl)amino]pyrimidine-4-carboxylate. The crude mixture was dissolved in a mixture of THF/EtOH/H2O (3/2/1, 84 mL) and treated with an aqueous solution of lithium hydroxide (1N, 16 mL, 16 mmol). The reaction mixture was stirred at RT for 60 minutes. Water was added (50 mL) and the aqueous layer was washed with chloroform. and the aqueous layer was washed with DCM (30 mL). The aqueous layer was acidified to pH 5 by addition of an HCl solution (1N). A precipitate was formed, which was filtered to afford the title compound.

Provenance & Evidence