Lithium hydroxide, monohydrate → 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

To a solution of 5-fluoro-3-phenyl-2-{(S)-1-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-ylamino]ethyl}-3H-benzoimidazole-4-carboxylic acid methyl ester (1.34 g, 2.66 mmol) in methanol (40 mL) and water (4 mL) was added lithium hydroxide monohydrate (0.166 g, 15. 9 mmol) and the reaction mixture heated at 80° C. for 16 h. The reaction mixture was concentrated in vacuo to remove methanol and the residual aqueous solution acidified to ph˜4 by addition of HCl (1 M) causing a precipitate to form. The product was collected by filtration and dried in vacuo to give the title compound as an off white solid (564 mg, 43%). LCMS (Method C): RT=2.44 min, [M+H]+=502.

Provenance & Evidence