Hydrochloric Acid → HCID 68158153, compound

Participants

Reaction Steps

{(S)-1-[4-Fluoro-2-(pyrimidin-4-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (0.27 g, 0.72 mmol) was treated with 4M HCl in dioxane (10 mL) for 45 min at 20° C. The solvent was removed by evaporation under reduced pressure to give a solid, (0.29 g). 0.145 g of this solid was treated in a sealed tube with 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (103 mg, 0.43 mmol) and DIPEA (0.25 mL), 1.44 mmol) in IPA (1.5 mL) at 80° C. under argon for 16 h. The reaction mixture was diluted with EtOAc (20 mL) and washed with water (5 mL). The aqueous layer was extracted with EtOAc (10 mL). The combined organic extracts were dried (Na2SO4), concentrated in vacuo and purified by column chromatography (Si—PCC, gradient 0-10% (9:1 MeOH/0.880 NH3) in DCM) to give the title compound as an orange gum, (88 mg, 51%). LCMS (Method B): RT 1.99 min [M+H]+ 478.13

Provenance & Evidence