Diisopropylethylamine → 2-methoxy-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)nicotinamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-phenylimidazo[1,2-a]pyrimidin-7-amine (200 mg, 951 μmol, Eq: 1.00), 2-methoxynicotinic acid (146 mg, 951 μmol, Eq: 1.00), diisopropylethylamine (369 mg, 498 μl, 2.85 mmol, Eq: 3) and propylphosphonic anhydride in ethyl acetate 50% (1.21 g, 1.12 ml, 1.9 mmol, Eq: 2) in tetrahydrofuran (10 ml) is stirred for 18 hours at 60° C. The mixture is diluted with ethyl acetate and washed 2 times with water and once with brine, the organic layer was separated, dried over magnesium sulfate, filtrated and evaporated. The crude material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using ethyl acetate/methanol 0-10% as eluent affording 2-methoxy-N-(2-phenylimidazo[1,2-a]pyrimidin-7-yl)nicotinamide (36 mg, 11%) as a light yellow solid. MS: m/e=346.1 (M+H+), mp: 225-226° C.

Provenance & Evidence