Potassium Carbonate → HCID 22473448, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(3-bromophenyl)-5-cyano-3,6-dihydro-4-methyl-2-oxo-(2H)-pyrimidine (1.62 g, 5.5 mmol), pyridine-4-boronic acid (0.75 g, 6.1 mmol), potassium carbonate (2.28 g, 16.5 mmol) and DMF (10 mL) was flushed with nitrogen gas several times before [1,1′-bis(diphenylphsophino)ferrocene]dichloropalladium (50 mg) was introduced. The reaction mixture was heated at 95° C. under nitrogen for 64 h, cooled to room temperature and filtered through Celite. The filtrate was diluted with MeOH and stirred with AG 50W-X2 Resin for 10 min. The resin was collected by vacuum filtration, washed with MeOH and then eluted with 2 M NH3 in MeOH. This NH3-MeOH solution was concentrated in vacuo to give 5-cyano-3,6-dihydro-4-methyl-2-oxo-6-(3-(4-pyridyl)phenyl)-(2H)-pyrimidine as a brown solid (1.6 1 g; 32%): 1H NMR (DMSO-d6, 400 MHz) δ 9.58 (s, 1H), 8.66 (d, 2H, J=2.2 Hz), 7.88 (s, 1H), 7.77 (d, 1H, J=7.9 Hz), 7.69 (m, 3H), 7.57 (m, 1H), 7.41 (d, 1H, J=7.9 Hz), 5.22 (s, 1H), 2.03 (d, 3H, J=2.2 Hz).

Provenance & Evidence