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

HRID 507663
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HRID 507663 반응식
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
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6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 684631243-(Dimethylamino)-2-phenyl-1-(thiophen-2-yl)prop-2-en-1-oneHCID 178479475HCID 178479475, 화합물

생성물 1

HCID 602045701-(2-(5-Phenyl-4-(thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

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온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-de10ea82628f41f1a2e9289944b7bf1f
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786132B2

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