Potassium Phosphate, Tribasic → 7-Methyl-3-[3'-(5-methyl-[1,2,4]oxadiazol-3-yl)biphenyl-3-yl]imidazo[1,2-a]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 7-methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyrimidine (0.1 g, 0.29 mmol) in 1,4-dioxane (3 ml) was added 3-(3-bromophenyl)-5-methyl-[1,2,4]oxadiazole (0.142 g, 0.59 mmol) (prepared as described in WO 95/27692), potassium phosphate (189 mg, 0.89 mmol) and tetrakis(triphenylphosphine)palladium(0) (17 mg, 15 μmol) and the mixture heated at 90° C. for 18 h. After cooling to ambient temperature the solvent was evaporated in vacuo and the residue stirred with 10% methanol in dichloromethane. The solid material was removed by filtration and the filtrate applied to two preparative TLC plates (silica gel) and eluted with 5% methanol in dichloromethane. The appropriate band was collected and processed, affording a solid which was recrystallised from dichloromethane/ethyl acetate/isohexane to give 7-methyl-3-[3′-(5-methyl-[1,2,4]oxadiazol-3-yl)biphenyl-3-yl]imidazo[1,2-a]pyrimidine as a cream coloured solid (32 mg): δH (400 MHz, CDCl3) 2.67 (3H, s), 2.68 (3H, s), 6.79 (1H, d, J 7), 7.60-7.80 (5H, m), 7.87 (1H, s), 7.92 (1H, m), 8.10 (1H, dd, J 7 and 1), 8.32 (1H, s), 8.52 (1H, d, J 7); m/z (ES+) 368 (M++H).

Provenance & Evidence