Dibutyltin dichloride → HCID 66665218, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 4-(2-(3-aminophenyl)-5-oxo-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate (60 mg, 0.140 mmol, 1.0 equiv) and 4-pyridinecarboxaldehyde (0.013 mL, 0.140 mmol, 1.0 equiv) in 1 mL tetrahydrofuran in a microwave vial is added dibutyltin dichloride (4.25 mg, 0.014 mmol, 0.1 equiv) and Phenylsilane (0.035 mL, 0.280 mmol, 2.0 equiv). The mixture is heated in a microwave reactor for 10 min at 100° C. Upon completion, the reaction mixture is filtered through a thiol-SPE column (Stratospheres) and concentrated in vacuo to give crude tert-butyl 4-(5-oxo-2-(3-(pyridin-4-ylmethylamino)phenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)piperazine-1-carboxylate as a yellow oil. The residue is then taken on crude to the next reaction, which followed the same procedure as above to give 7-(piperazin-1-yl)-2-(3-(pyridin-4-ylmethylamino)phenyl)-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (10 mg, 18%) as a white solid.

Provenance & Evidence