Hydrochloric Acid → 5-Fluoro-3-phenyl-2-{(S)-1-[9-(tetrahydropyran-2-yl)-9H-purin-6-ylamino]ethyl}-3H-benzoimidazole-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 5-fluoro-3-phenyl-2-{(S)-1-[9-(tetrahydropyran-2-yl)-9H-purin-6-ylamino]ethyl}-3H-benzoimidazole-4-carboxylic acid methyl ester (580 mg, 1.13 mmol) and LiOH.H2O (94 mg, 2.25 mmol) in MeOH (20 mL) and water (2 mL) was heated at 45° C. for 3 h. Additional LiOH.H2O (94 mg) was added and the mixture heated at 80° C. for 16 h. After further addition of LiOH.H2O (94 mg), stirring at 75° C. was continued for 18 h. After cooling to RT, the pH of the mixture was adjusted to 4 by addition of 1N HCl. The organic solvent was removed under reduced pressure and EtOAc was added to the crude mixture. After sonication of the suspension, the organic solvent was removed in vacuo. The solid was collected by filtration and dried in vacuo to afford the title compound (412 mg, 73%). LCMS (Method C): RT 2.40 min [M+H]+ 502.0.

Provenance & Evidence