Potassium Carbonate → 1-(2-(5-Bromo-4-(thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

HRID 2267445

Reaction equation

[Br:1][C:2]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:20][CH2:21][CH2:22][N:23]1[CH2:27][CH2:26][NH:25][C:24]1=[O:28]>CN1CCCC1=O>[Br:1][C:2]1[C:3]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:5]([NH:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][NH:25][C:24]2=[O:28])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

5-Bromo-2-chloro-4-(thiophen-2-yl)pyrimidine (2.0 g, 7.25 mmol) dissolved in N-methyl pyrrolidone (25 mL) was treated with potassium carbonate (2 g, 14.5 mmol) and 1-(2-aminoethyl)imidazolidin-2-one (1.125 g, 8.71 mmol). The reaction was heated to 110° C. overnight. The reaction was poured into ice water and extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine and then dried with sodium sulfate. Purification was achieved by flash chromatography using a gradient of 0 to 10% methanol in dichloromethane to obtain a yellow solid. Yield=2 g. MS (M+H)+ 368/370.

Workup

extractionextracted with dichloromethane
washThe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
dry with materialdried with sodium sulfate
customPurification
customto obtain a yellow solid

Sources & evidence

ORD record: ord-db24c5c1e232476eaa24c1f47bdaadab
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Linked notes

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