Potassium Carbonate → HCID 86601382, compound

Participants

Reaction Steps

To a suspension of (NaH 60% in mineral oil, 169 mg, 4.23 mmol) in DME (10 mL) was added 2-hydroxypyridine (366 mg, 3.85 mmol). [Hydrogen evolution was observed]. Then, powdered K2CO3 (2.31 g, 19.2 mmol) was added followed by portion-wise addition of 2-amino-5-bromothiazole hydrobromide (1.00 g, 3.85 mmol). The mixture was refluxed with stirring for 16 h and allowed to cool down to room temperature, quenched with water and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and organic phase was extracted with HCl 1N. The acidic extract was neutralized with saturated NaHCO3 and the precipitate was extracted first with EtOAc and then with a mixture of MeOH/CHCl3 (20:85). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was crystallized by addition of a mixture of MeOH/CHCl3 (5:95) affording the title compound 170 (21 mg, 3%). 1H NMR: (CD3OD) δ (ppm): 9.05 (dd, J=7.2, 2.0 Hz, 1H), 8.70 (ddd, J=9.2, 6.7, 2.2 Hz, 1H), 8.44 (s, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.59 (bs, 2H), 7.58 (td, J=6.8, 1.4 Hz, 1H). m/z: 194.2 (MH+).

Provenance & Evidence