Water → 1-(2-(5-Phenyl-4-(thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

Temperature

100 °C

3-(Dimethylamino)-2-phenyl-1-(thiophen-2-yl)prop-2-en-1-one (1 g, 3.88 mmol) in N-methyl pyrrolidone (10 mL) was treated with 1-(2-(2-oxoimidazolidin-1-yl)ethyl)guanidine hydrochloride (1 M solution in N-methyl pyrrolidone 5.82 mL, 5.82 mmol) and cesium carbonate (1.26 g, 3.88 mmol). The mixture was heated at 100° C. overnight. The reaction was then allowed to cool to room temperature and poured into cold water. The aqueous layer was extracted three times with dichloromethane. All the organic layers were combined and washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, reduced in vacuo and purified by flash chromatography using a gradient of 0 to 10% methanol in dichloromethane to obtain a yellow solid. Yield=1.2 g. MS (M+H)+ 366.

1. temperatureto cool to room temperature
2. extractionThe aqueous layer was extracted three times with dichloromethane
3. washwashed with saturated aqueous sodium bicarbonate, water and brine
4. dry with materialThe organic layer was then dried with sodium sulfate
5. custompurified by flash chromatography
6. customto obtain a yellow solid

ORD record

ord-de10ea82628f41f1a2e9289944b7bf1f

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786132B2