Sodium ethoxide → HCID 118863131, compound

HRID 63909Notes

Reaction equation

HRID 63909 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][NH:7][C:8](=[O:19])[NH:9][C:10]1[S:11][CH:12]=[C:13]([CH3:18])[C:14]=1[C:15]([O-])=[O:16])[CH3:2].[O-]CC.[Na+]>CCO>[CH3:18][C:13]1[C:14]2[C:15](=[O:16])[N:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:20])[C:8](=[O:19])[NH:9][C:10]=2[S:11][CH:12]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 131737212HCID 131737212, compound

Product 1

HCID 118863131HCID 118863131, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-(3-(3-ethoxy-3-oxopropyl)ureido)-4-methylthiophene-3-carboxylate (470 mg, 1.5 mmol) in EtOH (10 mL) was added sodium ethoxide (203 mg, 2.19 mmol, freshly prepared). The reaction was heated at reflux for 4 h, concentrated, acidified with 1N HCl until PH=1 then extracted with EA (2×10 mL). The combined organic layers were dried over Na2SO4 and concentrated to give ethyl 3-(5-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (330 mg, 82% yield) as a yellow thick oil. LCMS: MH+ 255 and TR=0.718 min. Used without further purification.

Workup

  1. customfreshly prepared)
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 4 h
  4. concentrationconcentrated
  5. extractionthen extracted with EA (2×10 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e515f10b28cb49619eac15b384fdc244
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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