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

HRID 2267446Notes

Reaction equation

HRID 2267446 reaction equation
Br[C:2]1[C:3]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[N:6][CH:7]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[C:3]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)=[N:4][C:5]([NH:8][CH2:9][CH2:10][N:11]3[CH2:15][CH2:14][NH:13][C:12]3=[O:16])=[N:6][CH:7]=2)=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 742994-Chlorophenylboronic acidHCID 602045731-(2-(5-Bromo-4-(thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

Product 1

HCID 602045741-(2-(5-(4-Chlorophenyl)-4-(thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1-(2-(5-Bromo-4-(thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one (0.1 g, 0.27 mmol), 4-chlorophenylboronic acid (0.085 g, 0.54 mmol), sodium carbonate (0.27 mL of 2.0 M solution, 0.52 mmol) were added to a flask containing dioxane (1 mL). The flask was flushed with nitrogen and tetrakis(triphenylphosphine)palladium (0.062 g, 0.054 mmol) was added. The reaction was heated to 80° C. overnight. The reaction was cooled down to ambient temperature and diluted with ethyl acetate and water. The organic layer was filtered through a pad of celite and washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, concentrated and purified by column chromatography using a gradient 2 to 10% of methanol in dichloromethane to afford an off-white solid. Yield=0.04 g. MS (M+H)+ 400.

Workup

  1. additionwas added
  2. temperatureThe reaction was cooled down to ambient temperature
  3. filtrationThe organic layer was filtered through a pad of celite
  4. washwashed with saturated aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic layer was then dried with sodium sulfate
  6. concentrationconcentrated
  7. custompurified by column chromatography
  8. customto afford an off-white solid

Sources & evidence

ORD record
ord-9727dfe2feca4dd89ce10a3340f68918
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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