Cesium carbonate → HCID 57948947, compound

Participants

Reaction Conditions

Reaction Steps

To a 110° C. solution of (+/−) tert-butyl (4S,6S)-4-(3-bromophenyl)-6-(hydroxymethyl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-ylcarbamate (150 mg, 0.36 mmol) in 1,2-dimethoxyethane (4.5 mL), ethanol (1.5 mL), and water (2.3 mL) is added pyrimidine-5-boronic acid (112 mg, 0.90 mmoles, 2.5 equiv), cesium carbonate (353 mg, 1.08 mmol, 3 equiv), and bis(triphenylphosphine)palladium(II) chloride (25 mg, 0.036 mmol, 0.1 equiv). The reaction is stirred at 110° C. After 20 minutes, the reaction mixture is diluted with EtOAc and H2O. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue is purified by column chromatography on silica gel (5% MeOH/DCM) to give the title compound (29% yield): MS (m/z): 415 (M+1)

Provenance & Evidence