Lithium Hydroxide → N-[4-Amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-succinamic acid

Participants

Reaction Steps

To a solution of N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-succinamic acid methyl ester (0.54 g, 1.05 mmoles) in THF (20 ml) was added a solution of Lithium hydroxide (0.33 g, 13.8 mmoles) in water (10 ml). The mixture was stirred at room temperature for 4 hours, then concentrated under reduced pressure. The aqueous residue was pH adjusted to pH=8, washed with EtOAc, and lyophilized for 36 hours. The resulting solid was washed with 30% methanol in ethyl acetate, and filtered. The filtrate was evaporated and the residue was washed twice with dichloromethane, dissolved in water and pH adjusted pH=7 by addition of 0.5 N HCl aqueous solution. The resulting precipitate was recrystallized from water, and the crystals were washed with dichloromethane/ether to give 40 mg of N-[4-Amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-succinamic acid as a light yellow solid. MS (M+H)=501.

Provenance & Evidence