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Ethanol → 2-(2-(2-Oxoimidazolidin-1-yl)ethylamino)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidine-5-carbonitrile

HRID 2267437
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HRID 2267437 반응식
Br[C:2]1[S:6][C:5]([C:7]2[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([NH:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][NH:20][C:19]3=[O:23])[N:8]=2)=[CH:4][CH:3]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>ClCCl.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>[O:23]=[C:19]1[NH:20][CH2:21][CH2:22][N:18]1[CH2:17][CH2:16][NH:15][C:9]1[N:8]=[C:7]([C:5]2[S:6][C:2]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)=[CH:3][CH:4]=2)[C:12]([C:13]#[N:14])=[CH:11][N:10]=1
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참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 602045694-(5-Bromothiophen-2-yl)-2-(2-(2-oxoimidazolidin-1-yl)ethylamino)pyrimidine-5-carbonitrile

생성물 1

HCID 602045672-(2-(2-Oxoimidazolidin-1-yl)ethylamino)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidine-5-carbonitrile

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 6344Dichloromethane용매

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온도
130 °C

실험 절차

4-(5-Bromothiophen-2-yl)-2-(2-(2-oxoimidazolidin-1-yl)ethylamino)pyrimidine-5-carbonitrile (0.08 g, 0.2 mmol), thiophen-2-ylboronic acid (0.052 g, 04 mmol), sodium carbonate (1.5 mL of 2 M solution, 1 mmol) were added to a microwave tube containing ethanol (1.5 mL). The tube was flushed with nitrogen and tetrakis(triphenylphosphine)palladium (0.06 g, 0.054 mmol) was added. The tube was capped and heated to 130° C. for 30 min in a Personal Chemistry microwave. The reaction was diluted with dichloromethane 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 on silica gel using a gradient of 0 to 10% methanol in dichloromethane to afford a yellow solid which recrystallized from ethyl acetate. Yield=0.066 g. MS (M+H)+ 397.

후처리

  1. additionwas added
  2. customThe tube was capped
  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 on silica gel using a gradient of 0 to 10% methanol in dichloromethane
  6. customto afford a yellow solid which
  7. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-13821481fe2d4cca99d88871ec9c51f6
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07858785B2

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