Imidazole → HCID 136265184, compound

Participants

Reaction Steps

Three 5 mL microwave vials were charged 7-chloro-2-methyl-5-(4-morpholinyl)-3-(1-naphthalenylmethyl) pyrazolo[1,5-a]pyrimidine (50 mg, 0.127 mmol), imidazole (130 mg, 1.909 mmol), potassium iodide (42.3 mg, 0.255 mmol), copper(I) iodide (48.5 mg, 0.255 mmol) and palladium(II) acetate (8.57 mg, 0.038 mmol) in N,N-Dimethylformamide (DMF) (0.75 mL). The reaction was purged with nitrogen, sonicated for 3 min and subjected to microwave irradiation at 185° C. for 10 min. The reactions were combined and filtered through a pad of celite. The filter pad was washed with DCM (10 mL×4), and the filtrate was concentrated. Two products with same molecular weight were detected. The residue was purified by reversed phase HPLC (10˜90% CH3CN (0.1% TFA)/Water (0.1% TFA)) to give the product (18 mg, 11%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.34 (s, 3H) 3.68 (m, 4H) 3.70-3.76 (m, 4H) 4.39 (s, 2H) 7.17-7.55 (m, 7H) 7.77 (d, J=8.08 Hz, 1H) 7.86-7.94 (m, 1H) 8.45-8.53 (m, 1H) 12.95 (s, 1H); LC/MS: MS (ES+) m/e 425.0 [M+H]+.

Provenance & Evidence