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

Participants

Reaction Steps

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 (160 mg, 0.241 mmol) and 2-methoxyethanol (95 μL, 1.21 mmol) were dissolved in THF (10 mL). Sodium hydride (96 mg, 2.41 mmol) was added portion-wise and the mixture stirred under argon at rt for 1 h. The mixture was then diluted with EtOAc (50 mL), carefully quenched with saturated aqueous NH4Cl, washed with water, brine and separated. The organic fraction was dried (Na2SO4), concentrated under reduced pressure and the resulting solid residue purified by flash column chromatography (40 g GraceResolv, silica cartridge) eluting with 50-100% EtOAc/heptane to afford the desired compound (86 mg, 58%) as a colourless resin. MS: 612.16 [M+H]+.

Provenance & Evidence