Water → 2-Anilino-4-(1-ethyl-2,4dimethylimidazol-5-yl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

5-(3-Dimethylaminoprop-2-en-1-oyl)-1-ethyl-2,4-dimethylimidazole (Method 10; 5.65 g, 25.6 mmol), phenylguanidine hydrogen carbonate (6.05, 30.7 mmol) and sodium methoxide (3.47 g, 64.2 mmol) were suspended in anhydrous DMA (80 ml) and the mixture heated at 150° C. for 18 hours. The reaction mixture was allowed to cool to ambient temperature and poured into water (50 ml). The solution was extracted EtOAc (2×50 ml). The combined extracts were washed with water (2×50 ml) and then brine (2×50 ml), dried and the volatiles removed by evaporation. The residue purified by flash silica chromatography DCM:MeOH (increasing in polarity from 100:0 to 96:4) to give the title compound (5.2 g, 70%) as an orange oil. NMR: 1.06 (t, 3H), 2.22 (s, 3H), 2.34 (s, 3H), 4.32 (q, 2H), 6.83 (d, 1H), 6.97 (t, 1H), 7.28 (t, 2H), 7.70 (d, 2H), 8.43 (d, 2H), 9.40 (s, 1H); m/z 294.

Provenance & Evidence