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

HRID 2267455Notes

Reaction equation

HRID 2267455 reaction equation
[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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-78aea74151a14261a4a7af8905bb55d1
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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