Triethylamine → Racemic 3-(10-(4-chlorothiazol-2-yl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

Trifluoromethanesulfonic anhydride (3.95 ml, 23.41 mmol) was added dropwise to a solution of 3-(6-(4-(4-chlorothiazol-2-yl)-4-hydroxybutyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (5 g, 10.64 mmol) and triethylamine (3.56 ml, 25.5 mmol) in DCM (213 mL) at −78° C. The mixture was stirred for 1 min at −78° C. The reaction was quenched with saturated aqueous NaHCO3(aq) (100 mL) and extracted with DCM (3×100 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under reduced pressure to afford crude racemic 3-(10-(4-chlorothiazol-2-yl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,7,8,9,10-octahydropyrimido[4,5-a]indolizin-5-yl)benzonitrile.

Provenance & Evidence