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

HRID 2267448Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:9]2[S:10][C:11]([Cl:14])=[CH:12][CH:13]=2)=[N:4][C:5](Cl)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:21][CH2:22][CH2:23][N:24]1[CH2:28][CH2:27][NH:26][C:25]1=[O:29].C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[Br:1][C:2]1[C:3]([C:9]2[S:10][C:11]([Cl:14])=[CH:12][CH:13]=2)=[N:4][C:5]([NH:21][CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

5-Bromo-2-chloro-4-(5-chlorothiophen-2-yl)pyrimidine (0.4 g, 1.3 mmol), N-methyl pyrrolidone (3 mL), potassium carbonate (0.358 g, 2.6 mmol) and 1-(2-aminoethyl)-imidazolidin-2-one (0.2 g, 1.54 mmol) were all placed in a microwave tube. The reaction was heated to 150° C. for 20 min in a Personal Chemistry microwave. A saturated solution of sodium bicarbonate was added to the reaction mixture, which was extracted three times with dichloromethane. The organic layer was dried with sodium sulfate and purified by flash chromatography on silica gel using gradient of 0 to 10% methanol in dichloromethane to obtain a white solid. Yield=0.41 g. MS (M+H)+ 402/404.

Workup

customall placed in a microwave tube
extractionwas extracted three times with dichloromethane
dry with materialThe organic layer was dried with sodium sulfate
custompurified by flash chromatography on silica gel using gradient of 0 to 10% methanol in dichloromethane
customto obtain a white solid

Sources & evidence

ORD record: ord-0f717531a48746a4a235f3e34b342912
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858785B2

Reaction notes

Loading…