Potassium Carbonate → HCID 67983634, compound

Participants

Reaction Steps

A solution of N′-{5-[(2E)-3-(dimethylamino)prop-2-enoyl]-4-methylpyrimidin-2-yl}-N,N-dimethylimidoformamide (27) (50 mg, 0.191 mmol), 1-(4-fluorophenyl)guanidine hydrochloride (102 mg, 0.383 mmol), and K2CO3 (106 mg, 0.765 mmol) in DMF (1018 μl) was heated at 120° C. for 2 d. The crude product was filtered through a syringe filter, then the crude product was purified by reverse-phase HPLC [30-100% organic phase over 15 minutes] to obtain ˜80% pure desired product. The product was taken up in 10% MeOH/DCM, then was purified by Biotage™ silica gel chromatography [10 g SNAP column, 2-10% MeOH/DCM] and further purified by trituration with acetone and acetonitrile to obtain the desired product as a pale yellow solid (10.23 mg, 18% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.47 (s, 3H) 6.93 (s, 2H) 7.02 (d, J=5.05 Hz, 1H) 7.12 (t, J=8.84 Hz, 2H) 7.77 (dd, J=9.35, 4.80 Hz, 2H) 8.44 (s, 1H) 8.46 (d, J=5.05 Hz, 1H) 9.61 (s, 1H). HRMS (ES+) for C15H13FN6.H+ [MH+]: calcd, 297.1264; found, 297.1274. UV-LC: 98.95/100% UV purity at 214/254 nm; tR=4.30 minutes over 7.75 minutes.

Provenance & Evidence