Ammonium formate → HCID 118699713, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-Chloro-6,7,8,9-tetrahydrothieno[3,2-c]-2,7-naphthyridine (3.22 g, 14.33 mmol), 10% Pd on C (500 mg) and ammonium formate (8.13 g, 128.97 mmol) in EtOH (125 ml) was heated at 80° C. for 24 hours. Analytical data (TLC, MS) confirmed complete removal of chlorine to give both the title compound along with the N-formyl analog. Upon cooling, the catalyst was filtered off (celite) and the filtrate was treated with NaOH(aq.) until pH ˜14. The alkaline reaction mixture was refluxed for 33 hours, cooled, filtered and concentrated. Elution through a flash column (silica gel 60, 230-400 mesh, 9:1 EtOAc:7M NH3 in MeOH) gave the title compound as a viscous yellow oil which crystallized on standing (1.96 g, 72%).

Provenance & Evidence