Sodium hydride → HCID 24898953, compound

Participants

Reaction Steps

To a 20 mL vial was added (1,4-dimethyl-1H-imidazol-5-yl)methanol (32 mg, 0.26 mmol), NaH (10 mg, 60% in oil, 0.12 mmol) and 4 mL of DMF. The reaction mixture was stirred at room temperature for 30 minutes, at which time the reaction was cooled to 0° C., the crude intermediate 2-(5-butyl-4-(chloromethyl)-1H-pyrazol-1-yl)-5-methyl-4-(thiophen-2-yl)pyrimidine (60 mg, 0.17 mmol) was added, warmed to room temperature and stirred for an additional 2 hours. The crude reaction was partitioned between water and EtOAc, the organic layer was concentrated and was purified by reverse phase preparative HPLC to provide 1.4 mg of 24 as a clear film. 1H NMR (400 MHz, MeOD-d3) δ 0.851 (t, J=5.9 Hz, 3H), 1.35 (q, J=5.9 Hz, 2H), 1.57 (t, J=6.2 Hz, 2H), 2.38 (s, 3H), 2.67 (s, 3H), 3.35 (t, J=4.8 Hz, 2H), 3.91 (s, 3H), 4.61 (s, 2H), 4.67 (s, 2H) 7.31 (t, J=3.6 Hz, 1H), 7.76 (s, 1H), 7.78 (d, J=4.1 Hz, 1H), 7.96 (d, J=3.1 Hz, 1H), 8.71 (s, 1H), 8.81 (s, 1H). LCMS (ES+) m/z 437 (M+1).

Provenance & Evidence