N,N,N',N'-Tetramethylethylenediamine → 2-(2-Ethylbenzoimidazol-1-yl)-8-iodo-9-methyl-6-morpholin-4-yl-9H-purine

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine (1.67 g, 4.58 mmol) and TMEDA (1.0 mL, 799 mg, 6.88 mmol) in THF (25 mL) was cooled to −78° C. before the drop wise addition of n-BuLi (2.8 mL, 6.88 mmol, 2.5 M solution in hexanes). The resulting mixture was stirred for 40 mins before the addition of 1-chloro-2-iodoethane (629 μL, 1.3 g, 6.88 mmol). The resulting mixture was stirred at −78° C. for 1 h then quenched with H2O and warmed to r.t. The pale yellow precipitate was collected by filtration washing with further H2O and dried under vacuum at 50° C. 2-(2-Ethylbenzoimidazol-1-yl)-8-iodo-9-methyl-6-morpholin-4-yl-9H-purine was afforded as a pale yellow powder (2.0 g, 90%). LCMS (method H): RT 2.74 min [M+H]+ 490.2

Provenance & Evidence