Ethyl butyrate → 5-Ethyl-2-thiouracil

HRID 705851Notes

Reaction equation

HRID 705851 reaction equation
CC(C)([O-])C.[K+].[C:7]([O:12]CC)(=O)[CH2:8][CH2:9][CH3:10].[CH:15](OCC)=O.[NH2:20][C:21]([NH2:23])=[S:22]>C1COCC1.C(OCC)C.O.CC(O)=O>[CH2:9]([C:8]1[C:7](=[O:12])[NH:20][C:21](=[S:22])[NH:23][CH:15]=1)[CH3:10]

Participants

9

Reactant 4

HCID 7762Ethyl butyrateHCID 8025Ethyl formateHCID 2723790ThioureaHCID 23665647Potassium tert-butoxide

Product 1

HCID 30020425-Ethyl-2-thiouracilYield 82%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of potassium tert-butoxide (12.08 g, 108 mmol) in THF (40 mL) was added a solution of ethyl butyrate (5.69 mL, 43.0 mmol) and ethyl formate (6.93 mL, 86 mmol) in diethyl ether (40.0 mL) dropwise under nitrogen. The mixture was stirred at room temperature for 3 h. After removing the solvent, the residue oil was dissolved in isopropanol (350 mL), and thiourea (6.55 g, 86 mmol) was added. The mixture was stirred at reflux overnight, and then concentrated in vacuo to get a solid. The solid was dissolved in water, adjusted pH to 4 with AcOH, and extracted by DCM. The organic layer was dried over Na2SO4, filtered and concentrated to afford the title compound (5.5 g, 82% yield) as a pink solid.

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue oil was dissolved in isopropanol (350 mL)
  3. stirringThe mixture was stirred
  4. temperatureat reflux overnight
  5. concentrationconcentrated in vacuo
  6. customto get a solid
  7. extractionextracted by DCM
  8. dry with materialThe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-267e12404e0a49179f013a737b5f339a
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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