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

HRID 507669

反応式

HRID 507669 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d2b24887d45b4aada96961304afc37e2
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

関連ノート

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