Monomethyl terephthalate → Methyl 4-(1-(7-(5,6-dimethoxypyridin-2-ylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)benzoate

Participants

Reaction Steps

To a stirred solution of 5-(3-aminopyrrolidin-1-yl)-N-(5,6-dimethoxypyridin-2-yl)thiazolo[5,4-d]pyrimidin-7-amine hydrochloride (283 mg, 0.69 mmol), 4-(methoxycarbonyl)benzoic acid (161 mg, 0.89 mmol) in 10 mL of DMF were added HATU (340 mg, 0.89 mmol), DIEA (267 mg, 2.07 mmol), EDCI (145 mg, 0.759 mmol) and DMAP (93 mg, 0.76 mmol) at room temperature. Then the reaction mixture was stirred at room temperature for 24 hours. The solvent was evaporated at 80° C. at reduced pressure and the residue was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with a mixture of dichloromethane and methanol (20:1)) to give methyl 4-(1-(7-(5,6-dimethoxypyridin-2-ylamino)thiazolo[5,4-d]pyrimidin-5-yl)pyrrolidin-3-ylcarbamoyl)benzoate (350 mg, 94%) as a yellow solid. LC-MS: 536.1 [M+H]+, tR=1.68 min.

Provenance & Evidence