Imidazole → Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(iodomethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Participants

Reaction Steps

Imidazole (75 mg, 1.09 mmol), triphenylphosphine (276 mg, 1.05 mmol) and iodine (267 mg, 1.05 mmol) were dissolved in CH2Cl2 (15 mL) and stirred at rt for 5 mins. A solution of ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(hydroxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (485 mg, 0.88 mmol) in CH2Cl2 (10 mL) was then added and the mixture stirred at rt for 2 h. The mixture was pre-adsorbed onto silica gel and purified by flash column chromatography (80 g GraceResolv silica cartridge—dry loaded) eluting with 25-100% EtOAc/heptane to afford the desired compound (323 mg, 56%) as a pale yellow foam. MS: 664.02 [M+H]+.

Provenance & Evidence