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

HRID 507678ノート

反応式

HRID 507678 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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), 3.68mmol) 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.

後処理

  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

出典と根拠

ORDレコード
ord-8979ffcb32d14b2cb853211be7a9a425
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

反応ノート

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