N,N,N',N'-Tetramethylethylenediamine → 4-[2-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbonyl]piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine (500 mg, 1.38 mmol) and TMEDA (312 μL, 2.07 mmol) in THF (10 mL) at −78° C. was added n-BuLi (660 μL, 1.65 mmol, 2.5M solution in hexanes) and the resulting mixture stirred for 30 min before the addition of a solution of 4-(methoxymethylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester (564 mg, 2.07 mmol) in THF (5 mL) The resulting mixture was stirred for 2 h then quenched with H2O and extracted with EtOAc. The combined organic phases were dried (MgSO4) and concentrated in vacuo. The resulting residue was triturated with EtOAc:cyclohexane and the mother liquors concentrated in vacuo affording the title compound as an oil (760 mg, 96%). LCMS (method A): RT 3.67 min [M+H]+ 557.3

Provenance & Evidence