Hydrochloric Acid → 4-[(5-{3-Methyl-5-[(4-methylpyrimidin-2-yl)amino]phenyl}-1,3-thiazol-2-yl)methyl]cyclohexanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Ethyl 4-[(5-{3-methyl-5-[(4-methylpyrimidin-2-yl)amino]phenyl}-1,3-thiazol-2-yl)methyl]cyclohexanecarboxylate (147 mg, 0.326 mmol) was suspended in methanol (2.0 mL) in a microwave vial, and sodium hydroxide (1M in water, 0.652 mL, 0.652 mmol) was added. The reaction was heated to 110° C. for 30 min via microwave irradiation. The reaction was acidified to pH=3-4 with aqueous 1M HCl and extracted with 15% isopropyl alcohol in chloroform (2×). The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure to afford 4-[(5-{3-methyl-5-[(4-methylpyrimidin-2-yl)amino]phenyl}-1,3-thiazol-2-yl)methyl]cyclohexanecarboxylic acid as an off-white solid in a 2.5:1 mixture of diastereomers.

Provenance & Evidence