Pyrazole → HCID 59729280, compound

Participants

Reaction Steps

In a sealed tube 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl chloride 5 (2.0 g, 8.9 mmol), pyrazole (1.8 g, 26.5 mmol) and 1,4 dioxane (10 mL) were heated at 138° C. for 2 h. Upon cooling to ambient temperature a precipitate formed which was collected and washed with saturated aqueous NaHCO3 and diethyl ether to yield 49 (340 mg, 1,3 mmol) as a white solid. The filtrate was treated with saturated aqueous NaHCO3 (20 ml) and the resulting precipitate was washed with saturated aqueous NaHCO3 and diethyl ether to yield additional 49 (2.0 g, 7.8 mmol, 99% total yield). 1H NMR: (500 MHz, CD3OD) δ 8.99 (br s, 1H), 8.78 (br s, 1H), 8.29 (s, 1H), 8.06 (br s, 1H), 6.72 (br s, 1H), 4.30 (q, J=7.0 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H); LC/MS: (ES+) m/z (M+H)+=258; HPLC Rt=1.20 min., column L.

Provenance & Evidence