Methyl Acrylate → (E)-3-(2-amino-4-furan-2-yl-6-methylsulfanyl-pyrimidin-5-yl)-acrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of 457 mg (1,37 mmol) 4-furan-2-yl-5-iodo-6-methylsulfanyl-pyrimidin-2-ylamine, 0.25 ml (2.77 mmol) methyl acrylate, 96 mg (0.14 mmol) bis(triphenylphosphine)palladium(II) chloride and 0.67 g (2.06 mmol) cesium carbonate in 5 ml dioxane under argon in a sealed tube was heated at 100° C. for 16 h. After cooling to room temperature, the mixture was diluted with 50 ml ethyl acetate, filtered, and the filtrate was concentrated in vacuo. Flash chromatography (1/2-1/1 ethyl acetate/hexane) followed by trituration in ether/pentane afforded 194 mg (49%) (E)-3-(2-amino-4-furan-2-yl-6-methylsulfanyl-pyrimidin-5-yl)-acrylic acid methyl ester as an off-white crystalline solid. ES-MS m/e (%): 292 (M+H+, 100).

Provenance & Evidence