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

Participants

Reaction Conditions

Reaction Steps

In a 20 mL microwave vial was placed 8-(6-chloro-2-(4-nitrophenyl)pyrimidin-4-yl)-3-oxa-8-azabicyclo[3.2.1]octane (36, 500 mg, 1.442 mmol) in toluene (15 ml) to give a yellow suspension. The mixture was degassed with a stream of nitrogen and tributyl(3,6-dihydro-2H-pyran-4-yl)stannane (646 mg, 1.730 mmol) and Pd(PPH3)4 (167 mg, 0.144 mmol) were added. The reaction mixture was heated under microwave irradiation at 150° C. for 1 hour. The mixture was concentrated and the crude product was added to a silica gel column and was eluted with ethyl acetate in hexanes (25-70%). Collected fractions were concentrated to give 373 mg of a yellow solid. HRMS: 395.1707 [M+H]+. For [M+H]+ mass error=−0.6 mDa or −1.51 ppm.

Provenance & Evidence