N,N'-Dimethylethylenediamine → HCID 70981033, compound

Participants

Reaction Conditions

Reaction Steps

Into a reaction tube were placed CsF (211 mg, 1.4 mmol, 2.5 equiv), CuI (21 mg, 0.11 mmol, 0.2 equiv), 1-chloro-4-iodo-benzene (200 mg, 0.85 mmol, 1.5 equiv), (3-cyclohexyl-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl)-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (280 mg, 0.56 mmol, 1.0 equiv) and N,N′-dimethyl-ethylene diamine (60 μL, 0.56 mmol, 1.0 equiv). The tube was sealed, evacuated and back-filled with nitrogen 3 times, then THF (5 mL) was added and the reaction mixture was heated at 80° C. overnight. Further CuI (21 mg, 0.11 mmol, 0.2 equiv) and N,N′-dimethyl-ethylene diamine (30 μL, 0.28 mmol, 0.5 equiv) were added and the heating was continued for 24 h. The reaction mixture was cooled, diluted with EtOAc and the reaction was quenched with saturated ammonium chloride. The products were extracted with ethyl acetate, the combined organic extracts were washed with brine, dried (MgSO4), filtered and the solvent evaporated. The crude material was purified by column chromatography (SiO2, eluted with petrol—EtOAc 0-500%) to afford [1-(4-chloro-phenyl)-3-cyclohexyl-2-oxo-1,2,3,4-tetrahydro-pyrido[3,2-d]pyrimidin-6-yl]-(2,4-dimethoxy-benzyl)-carbamic acid tert-butyl ester (224 mg). MS: [M+H]+=606.

Provenance & Evidence