Ethanol → HCID 57948930, compound

Participants

Reaction Steps

To a 100° C. solution of tert-butyl (4S,6R)-4-(3-bromophenyl)-4,6-dimethyl-5,6-dihydro-4H-1,3-thiazin-2-ylcarbamate in 1,2-dimethoxyethane: water: ethanol [(3:1.5:1), 12 mL] is added, in a single portion, pyrimidine-5-boronic acid (128 mg, 5.9 mmoles, 2.5 equiv), bis(triphenylphosphine)palladium(II) chloride (29 mg, 41 μmoles, 0.1 equiv) and cesium carbonate (1.24 g, 1.24 mmoles, 3 equiv). After 20 minutes, the reaction is cooled to ambient temperature, diluted with water, and extracted with dichloromethane. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash column chromatography eluting with a linear gradient of hexane to hexane:ethyl acetate (5:2) over 20 minutes to give the title compound (39% yield): MS (m/z): 399 (M+1).

Provenance & Evidence