8-(Benzyloxy)-5-bromoimidazo[1,2-a]pyridine → {1-[2-(8-Benzyloxyimidazo[1,2-a]pyridin-5-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]piperidin-4-yl}dimethylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of dimethyl-[1-(4-morpholin-4-yl-2-(tributylstannanyl)thieno[3,2-d]pyrimidin-6-ylmethyl)piperidin-4-yl]amine (230 mg, 0.35 mmol), 8-benzyloxy-5-bromoimidazo[1,2-a]pyridine (127 mg, 0.42 mmol), Pd(PPh3)4 (40 mg, 0.035 mmol) and copper(I) iodide (66 mg, 0.35 mmol) in dioxane (3 mL) was purged with argon gas then heated at 140° C., for 20 min, in a microwave reactor. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was washed with MeOH then the desired product was eluted with 2 M NH3 in MeOH. The appropriate fractions were combined and evaporated. The resulting residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 20:80) to give {1-[2-(8-Benzyloxyimidazo[1,2-a]pyridin-5-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl]piperidin-4-yl}dimethylamine as a white solid (189 mg, 92%). LCMS (Method H): RT 3.07 min; [M+H]+ 584

Provenance & Evidence