Acetic Acid → [4,6-Bis(dimethylamino)-2-{4-[4-(trifluoromethyl)benzamido]benzyl}-5-pyrimidinyl]acetic acid

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of [4,6-bis-dimethylamino-2-[4-(4-trifluoromethylbenzoylamino)-benzyl]pyrimidin-5-yl]acetic acid methyl ester (50 g, obtained according to step B) and lithium hydroxide monohydrate (6.3 g) in a mixture of 100 mL of tetrahydrofurane and 50 mL of methanol in a 1500 mL double jacketed vessel is heated to 60±5° C. over a period of 1 hour. Deionized water (75 mL) is slowly added. The obtained solution is stirred for 2 hours at 60±5° C. A solution of acetic acid (11.6 g) in 50 mL of methanol is added at 60±5° C. The resulting suspension is gradually cooled to 5±5° C. over a period of 2 hours and stirred at this temperature for another 30 minutes. The solid is filtered off, washed with 200 mL of methanol and dried in vacuo at 50° C. to yield [4,6-bis-dimethylamino-2-[4-(4-trifluoromethyl-benzoyl-amino)benzyl]pyrimidin-5-yl]acetic acid (compound of formula (I)) in an amount of 43.65 g (yield: 90%; HPLC-purity: 99.6%).

Provenance & Evidence