Lithium hydroxide, monohydrate → 4-{4-[4-(3-Methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid

Participants

Reaction Steps

To a suspension of 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-yl-amino}-cyclohexanecarboxylic acid ethyl ester (35.4 g, 70 mmol) in THF (180 mL) and MeOH (200 mL) was added a solution of LiOH-H2O (14.69 g) in H2O (150 mL). The resulting mixture was briefly heated in a steam bath and stirred at RT with a mechanical stirrer for 1 h to provide a light yellow solution. The reaction mixture was concentrated in vacuo and diluted with cold H2O and the pH was adjusted to 6 with 10% HCl. The resulting solid was filtered, washed several times with cold H2O and finally with EtOH at 0° C. The resulting solid product was then dried in vacuo to provide 4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclo-hexanecarboxylic acid (32.2 g, 97.4%).

Provenance & Evidence