Triethylamine → 2-Cyclopropylpyrimidin-4-amine

Participants

Reaction Steps

Cyclopropylcarbamidine hydrochloride (7.61 g) was dissolved in ethanol (125 mL) and triethylamine (19.35 mL) and 2-chloro-acrylonitrile (5.52 mL) were added. The resulting orange-yellow solution was refluxed for 30 minutes. The mixture was cooled and left in a refrigerator over night. The solid was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (ethyl acetate/methanol 9:1) to give 2-cyclopropyl-pyrimidin-4-ylamine (4.2 g) as a light brown solid that was still contaminated with an unidentified component, but used without further purification. 1H NMR (δ, DMSO-d6, product signals only): 7.88 (d, 1H), 6.64 (br s, 2H), 6.16 (d, 1H), 1.89-1.82 (m, 1H), 0.87-0.81 (m, 4H).

Provenance & Evidence