Tributylvinyltin → HCID 86732066, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidine (1-2) (5.2 g, 23.2 mmol) in degassed toluene (200 mL) under nitrogen was added tetrakis(triphenylphosphine)palladium(O) (1.3 g, 1.16 mmol) followed by tributyl(vinyl)tin (8.8 mL, 30.2 mmol) and the reaction was heated at 110° C. for 3 h. The solvent was concentrated in vacuo and the crude residue was purified by silica gel column chromatography (0-50% EtOAc/hexanes) to afford 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyrimidine (1-3) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.63 (s, 1H), 6.76 (dd, 1H, J=17.3, 10.6 Hz), 6.52 (br d, 1H, J=17.3 Hz), 5.72 (br d, 1H, J=10.6 Hz), 2.91 (s, 3H), 2.72 (s, 3H), 2.42 (s, 3H). MS m/z=216 (M+H).

Provenance & Evidence