3,5-Dimethylpyrazole → 2-Chloro-5-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-1,3-thiazole

Participants

Reaction Conditions

Reaction Steps

A solution of 3,5-dimethyl-1H-pyrazole (Aldrich, 114 mg, 1.190 mmol) in DMF (5 ml) was added over NaH (Aldrich, 34.3 mg, 1.42 mmol) at 0° C. under N2 atmosphere. The mixture was stirred during 5 min and 2-chloro-5-(chloromethyl)-1,3-thiazole (AK scientific, 200 mg, 1.19 mmol) in DMF (2 ml) was added. The mixture was allowed to stir overnight. Finally, it was heated to 50° C. for 1 h. DMF was eliminated by washing with 14 ml of a mixture EtOAc/NH4Cl 1N (1:1). The organic layer was dried over Na2SO4 and the solution concentrated to dryness under vacuum, to afford a crude product which was chromatographed (silica gel cartridge, Hex/EtOAc) yielding the title compound. 1H NMR (300 MHz, CDCl3) δ ppm: 7.37 (s, 1H); 5.82 (s, 1H), 5.26 (s, 2H); 2.24 (s, 3H); 2.22 (s, 3H). [ES+MS] m/z: 228.1 (MH+).

Provenance & Evidence