8-[6-(3,6-dihydro-2H-pyran-4-yl)-2-(4-nitrophenyl)pyrimidin-4-yl]-3-oxa-8-azabicyclo[3.2.1]octane → 4-[4-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-6-(tetrahydro-2H-pyran-4-yl)pyrimidin-2-yl]aniline

Participants

Reaction Steps

In a 250 mL round-bottomed flask was placed 8-(6-(3,6-dihydro-2H-pyran-4-yl)-2-(4-nitrophenyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (74, 353 mg, 0.895 mmol) in dichloromethane (10 mL) and 2-propanol (10 mL) to give a yellow solution. Pd—C (95 mg, 0.089 mmol) was added. The reaction mixture was stirred for 72 hours under an atmosphere of hydrogen. The reaction mixture was diluted with dichloromethane, filtered through Celite™ and washed with dichloromethane. The mixture was concentrated under reduced pressure to give 324 mg of a yellow solid. HRMS: 367.2130 [M+H+. For [M+H]+ mass error=0.3 mDa or 0.7 ppm.

Provenance & Evidence