Sodium Methoxide → HCID 67173009, compound

HRID 1891274Notes

Reaction equation

HRID 1891274 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]([CH2:13][C:14]([O:16]CC)=O)[C:10]([NH2:12])=[O:11])=[N:6][CH:7]=1.C[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[CH2:13][C:14](=[O:16])[NH:12][C:10]2=[O:11])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67172438HCID 67172438, compound

Product 1

HCID 67173009HCID 67173009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1-((5-Bromopyridin-2-yl)methyl)ureido)acetate (9J2) (35.0 mmol, 11.08 g) was dissolved in dry methanol (150 ml), and sodium methoxide (70.1 mmol, 3.79 g) added and the solution stirred at room temperature for 3 hours. The reaction was quenched with water and acidified with saturated ammonium chloride solution to ˜pH 7. The mixture was extracted with DCM (3×) and the combined organics washed with brine and dried over sodium sulphate, filtered and concentrated to afford a crude product which was purified on silica eluting with Heptane/EtOAc/EtOH 5/4/1 to give 1-((5-bromopyridin-2-yl)methyl)imidazolidine-2,4-dione. (9J3) 6.12 g (64%); 1H NMR (400 MHz, CDCl3) 8.68 (bs, 1H) 8.63 (d, 1H) 7.86 (dd, 1H) 7.22 (d, 1H) 4.61 (s, 2H) 4.04 (s, 2H).

Workup

  1. customThe reaction was quenched with water
  2. extractionThe mixture was extracted with DCM (3×)
  3. washthe combined organics washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a crude product which
  8. customwas purified on silica eluting with Heptane/EtOAc/EtOH 5/4/1

Sources & evidence

ORD record
ord-c53ebe82119247d6b17621011d177df3
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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