5-Bromopyrimidine → HCID 69514180, compound

Participants

Reaction Steps

To a mixture of 4-[(8-methyl-8-azabicylo[3.2.1]oct-3-yl)thio]phenyl trifluoromethanesulfonate (450 mg), 5-bromopyrimidine (187 mg), lithium chloride (150 mg) and tetrakis(triphenylphosphine) palladium (0) (68 mg) under nitrogen were added hexamethylditin (386 mg) and dioxane (15 ml). The mixture was heated under reflux overnight and then poured into a mixture of aqueous potassium fluoride (1.9 g in 13 ml water) and ethyl acetate (13 ml). This mixture was stirred vigorously for 2 hours, passed through a sintered funnel and the layers separated. The organic phase was washed with brine, dried (MgSO4), filtered and evaporated. The crude material was purified on an Isco CombiFlash device, followed by UV-guided LC to yield 8-methyl-3-{[4-(5-pyrimidinyl)phenyl]thio}-8-azabicyclo[3.2.1]octane (45 mg)

Provenance & Evidence