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

HRID 507663Notes

Reaction equation

CN(C)[CH:3]=[C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)=O.Cl.[O:20]=[C:21]1[NH:25][CH2:24][CH2:23][N:22]1[CH2:26][CH2:27][NH:28][C:29]([NH2:31])=[NH:30].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN1CCCC1=O>[C:12]1([C:4]2[C:5]([C:7]3[S:8][CH:9]=[CH:10][CH:11]=3)=[N:30][C:29]([NH:28][CH2:27][CH2:26][N:22]3[CH2:23][CH2:24][NH:25][C:21]3=[O:20])=[N:31][CH:3]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-de10ea82628f41f1a2e9289944b7bf1f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786132B2

Reaction notes

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