N,N-Dimethylethylenediamine → HCID 10452733, compound

Participants

Reaction Steps

A solution of 6-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pyridine-2-carboxylic acid (6-1, 100 mg, 0.32 mmol, 1 equiv), benzotriazole-1-yl-oxy-trispyrrolidinophosphonium hexafluorophosphate (197 mg, 0.73 mmol, 1.2 equiv), N,N-dimethylethylenediamine (70 μL, 0.63 mmol, 2 equiv) and N,N-diisopropylethyl-amine (20 μL, 0.73 mmol, 2.3 equiv) in DMF (5 mL) was stirred at 23° C. for 3 hours. The solution was partitioned between EtOAc (3×100 mL) and water (120 mL). The combined organic layers were washed with brine (200 mL), dried over sodium sulfate, then concentrated to afford N-[2-(dimethylamino)ethyl]-6-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)pyridine-2-carboxamide (6-2). 1H NMR (500 MHz, DMSO-d6) δ 10.21 (s, 1 H), 9.72 (s, 1 H), 9.42 (m, 1 H), 8.91 (s, 1 H), 8.47 (m, 1 H), 8.08 (m, 3 H), 7.48 (m, 2 H), 7.29 (m, 1 H), 3.73 (m, 2 H), 3.36 (m, 2 H), 2.89 (s, 3 H), 1.74 (s, 3 H).

Provenance & Evidence