2-Methyl-2-thiopseudourea → Ethyl-2-methylthio-4-methyl-5-pyrimidine carboxylate

HRID 41478Notes

Reaction equation

HRID 41478 reaction equation
[C:1]([C:4](=[CH:10]OCC)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].[NH2:14][C:15]([S:17][CH3:18])=[NH:16].C(N(CC)CC)C>CCO>[CH2:8]([O:7][C:5]([C:4]1[C:1]([CH3:2])=[N:14][C:15]([S:17][CH3:18])=[N:16][CH:10]=1)=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 51422-Methyl-2-thiopseudoureaHCID 8471TriethylamineHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl ester

Product 1

HCID 188208Ethyl-2-methylthio-4-methyl-5-pyrimidine carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Equimolar quantities of ethyl 2-acetyl-3-ethoxy-2-propenoate 1 (20.0 g, 107 mmol), ((amino(imino)methyl)-sulfanyl)methane 2 (9.68 g, 107 mmol) and triethylamine (10.8 g, 107 mmol) in EtOH (100 mL) were stirred at reflux for 48 hours. Then reaction mixture was concentrated and diluted with water. The biphasic mixture was transferred into a separatory funnel and extracted with DCM. Organic extract was washed with water, dried, filtered, and concentrated. The product was purified by crystallization from ethanol/water to yield in a colorless solid (18.4 g, 86.7 mmol, 81%).

Workup

  1. temperatureat reflux for 48 hours
  2. customThen reaction mixture
  3. concentrationwas concentrated
  4. additiondiluted with water
  5. customThe biphasic mixture was transferred into a separatory funnel
  6. extractionextracted with DCM
  7. extractionOrganic extract
  8. washwas washed with water
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe product was purified by crystallization from ethanol/water

Sources & evidence

ORD record
ord-d46d533018804057986b3e016decfa02
Source dataset
uspto-grants-2013_09
Patent number
US08530650B2

Reaction notes

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