Sodium hydride → 1-(2-(4-(Benzo[b]thiophen-2-yl)-5-bromopyrimidin-2-yloxy)ethyl)imidazolidin-2-one

HRID 2267455노트

반응식

HRID 2267455 반응식
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[O:9].[H-].[Na+].[S:12]1[C:16]([C:17]2[C:22]([Br:23])=[CH:21][N:20]=[C:19](Cl)[N:18]=2)=[CH:15][C:14]2[CH:25]=[CH:26][CH:27]=[CH:28][C:13]1=2>C1COCC1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[S:12]1[C:16]([C:17]2[C:22]([Br:23])=[CH:21][N:20]=[C:19]([O:1][CH2:2][CH2:3][N:4]3[CH2:8][CH2:7][NH:6][C:5]3=[O:9])[N:18]=2)=[CH:15][C:14]2[CH:25]=[CH:26][CH:27]=[CH:28][C:13]1=2

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 77290Hydroxyethyl imidazolidinoneHCID 574288214-(Benzo[b]thiophen-2-yl)-5-bromo-2-chloropyrimidine

생성물 1

HCID 602046301-(2-(4-(Benzo[b]thiophen-2-yl)-5-bromopyrimidin-2-yloxy)ethyl)imidazolidin-2-one

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

1-(2-Hydroxyethyl)imidazolidin-2-one (0.6 g, 4.6 mmol) was taken up in anhydrous THF (5 mL) and added dropwise to a reaction flask containing a suspension of sodium hydride (0.147 g (60% in oil), 3.68 mmol) in anhydrous THF (10 mL) at 0° C. The ice bath was removed and the reaction allowed to warm up to room temperature over a 2 h period. 4-(benzo[b]thiophen-2-yl)-5-bromo-2-chloropyrimidine (0.3 g, 9.2 mmol), dissolved in THF was added dropwise. The reaction was stirred overnight. The reaction was then diluted with ethyl acetate and saturated sodium bicarbonate. The organic layer was then washed with water and brine. The organic portion was dried with sodium sulfate and then purified by flash chromatography on silica gel using a gradient of 0 to 10% methanol in dichloromethane to give a white solid. Yield=0.085 g. MS (M+H)+ 420.

후처리

  1. additionadded dropwise to a reaction flask
  2. additioncontaining
  3. customThe ice bath was removed
  4. additionwas added dropwise
  5. washThe organic layer was then washed with water and brine
  6. dry with materialThe organic portion was dried with sodium sulfate
  7. custompurified by flash chromatography on silica gel using a gradient of 0 to 10% methanol in dichloromethane
  8. customto give a white solid

출처 및 근거

ORD 기록
ord-78aea74151a14261a4a7af8905bb55d1
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858785B2

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