N,N'-Dimethylethylenediamine → tert-Butyl {3-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-1-methyl-1H-imidazol-4-yl]phenyl}carbamate

Participants

Reaction Conditions

Reaction Steps

6-[4-(3-Iodophenyl)-1-methyl-1H-imidazol-5-yl]thieno[2,3-d]pyrimidin-4-amine (Example 49) (43 mg) was stirred with tert-butyl carbamate (24 mg), N,N′-dimethylethylenediamine (9 mg), copper(I) iodide (10 mg), and potassium phosphate (42 mg) in 1,4-dioxane (2 mL), degassed, and heated under an inert atmosphere at 100° C. for 24 hours. The mixture was partitioned between EtOAc and dilute aqueous NH3. The organic phase was dried and evaporated. The residue was purified by flash chromatography on silica using a gradient of 0-100% EtOAc in DCM then 0-20% MeOH in DCM as eluent. Fractions were evaporated to give the title compound as a gum (4 mg, 9%);

Provenance & Evidence