2,3-Dichloropyrazine → 4-(3-Chloropyrazin-2-yl)-2-methyl-6-(methylthio)pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,3-dichloropyrazine (0.034 mL, 0.228 mmol, Aldrich, St. Louis, Mo.), 2-methyl-4-(methylthio)-6-(tributylstannyl)pyrimidine (98 mg, 0.228 mmol) and tetrakis(triphenylphosphine)palladium (26.4 mg, 0.023 mmol, Strem Chemicals, Inc., Newburyport, Mass.) in toluene (2 mL) was stirred at 110° C. for 48 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with 20% EtOAc/CH2Cl2 to give 4-(3-chloropyrazin-2-yl)-2-methyl-6-(methylthio)pyrimidine (12 mg, 21% yield). 1H NMR (300 MHz, CDCl3) δ 8.63 (d, J=2.05 Hz, 1H); 8.47 (d, J=2.19 Hz, 1H); 7.44 (s, 1H); 2.77 (s, 3H); 2.56 (s, 3H). m/z (ESI, +ve ion) 253 (M+H)+.

Provenance & Evidence