Potassium Carbonate → 5-(Pyridin-2-ylsulfanyl)-thiazol-2-ylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-5-bromothiazole hydrobromide (1.00 g, 3.85 mmol) in DMF (8 mL) was added 2-mercaptopyridine (428 mg, 3.85 mmol) followed by addition of powdered K2CO3 (1.81 g, 15.09 mmol). The mixture was stirred at 80° C. for 1 h and at rt for 16 h. The solvent was removed in vacuo at 80° C. and the compound was partitioned between H2O and EtOAc. The aqueous layer was extracted with EtOAc and the organic phase was extracted with HCl 1N. The acidic extract was neutralized with saturated NaHCO3 and the precipitate was extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound 169 (589 mg, 73% yield). 1H NMR: (Acetone-d6) δ(ppm): 8.36 (s, 1H), 7.66 (s, 1H), 7.20 (s, 1H), 7.12-7.05 (m, 2H), 6.84 (s, 2H). m/z: 210.1 (MH+).

Provenance & Evidence