N,N,N',N'-Tetramethylethylenediamine → HCID 86667363, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)morpholine (1 g, 9 mmol) in THF (25 mL) at −78° C. was added Tetramethylethylenediamine (0.93 mL, 0.0062 mol) followed by 2.5 M of n-BuLi (2.5 mL, 0.0062 mol) dropwise. The reaction was stirred at −78° C. for 30 minutes and then ethyl trifluoroacetate (0.74 mL, 0.0062 mol) was added, continue stirred for 2 hours at −78° C. The reaction was quenched with water and extracted with EtOAc. The organic extracts were washed with water, brine, dried over MgSO4 and concentrated. The crude material was purified by ISCO with 0-100% EtOAc/hexane to give pure 1-(2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)-2,2,2-trifluoroethanone as a white solid (2.5 g, 70% yield). LC/MS (ESI+): m/z 421 (M+H)

Provenance & Evidence