N,N,N',N'-Tetramethylethylenediamine → 2-Chloro-8-iodo-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine (1.50 g, 4.63 mmol) and TMEDA (1.72 mL, 6.94 mmol) in THF (30 mL) was cooled to −78° C. before the drop wise addition of n-BuLi (6.08 mL, 9.73 mmol, 1.6 M solution in hexanes). The resulting mixture was allowed to stir at −78° C. for 485 min before the addition of 1-chloro-2-iodoethane (902 μL, 16.22 mmol). The resulting mixture was allowed to warm to 0° C. over 2.5 h then quenched with H2O and extracted with DCM. The combined organics were washed with brine then dried (Na2SO4) and concentrated in vacuo. The residue was triturated with iPrOAc and the resulting solid collected by filtration affording the title compound (1.80 g, 87%). LCMS (method A): RT 3.90 min [M+H]+ 450.3

Provenance & Evidence