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Ethyl 2-isocyanatopropionate → 5-Methyl-3-(2-(4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidine-2,4-dione

HRID 507560
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HRID 507560 반응식
[N:1]([CH:4]([CH3:10])[C:5]([O:7]CC)=O)=[C:2]=[O:3].[NH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:20]=[C:19]([C:21]2[S:22][C:23]([C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[CH:24][CH:25]=2)[CH:18]=[CH:17][N:16]=1>ClCCl>[CH3:10][CH:4]1[NH:1][C:2](=[O:3])[N:11]([CH2:12][CH2:13][NH:14][C:15]2[N:20]=[C:19]([C:21]3[S:22][C:23]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[CH:24][CH:25]=3)[CH:18]=[CH:17][N:16]=2)[C:5]1=[O:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 550681Ethyl 2-isocyanatopropionateHCID 60204267N-(2-aminoethyl)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-amine

생성물 1

HCID 602044425-Methyl-3-(2-(4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidine-2,4-dione수율 68.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethyl 2-isocyanatopropanoate (104 mg, 0.73 mmol) was added to a suspension of N-(2-aminoethyl)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidin-2-amine (200 mg, 0.66 mmol) in dichloromethane (10 mL) at rt and stirred for 8 h. The solid was filtered off and added to 15 mL of hydrochloric acid (5 M). After refluxing for 6 h, the mixture was cooled to rt and the precipitate was filtered off, washed with water and then dissolved in 10 mL of methanol. 50 mg of potassium carbonate was added and the mixture was stirred for 10 min. 20 mL of dichloromethane was added and the mixture was filtered through Celite. The filtrate was concentrated to give the title compound (180 mg, 68%). MS (M+H)+ 400.

후처리

  1. filtrationThe solid was filtered off
  2. additionadded to 15 mL of hydrochloric acid (5 M)
  3. temperatureAfter refluxing for 6 h
  4. filtrationthe precipitate was filtered off
  5. washwashed with water
  6. dissolutiondissolved in 10 mL of methanol
  7. addition50 mg of potassium carbonate was added
  8. stirringthe mixture was stirred for 10 min
  9. addition20 mL of dichloromethane was added
  10. filtrationthe mixture was filtered through Celite
  11. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-e379e529159e44e99136f3b6fb29751a
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786132B2

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