Triethylamine → Ethyl 4-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate

HRID 1893887Notes

Reaction equation

HRID 1893887 reaction equation
I.[NH2:2][CH:3]([S:10][CH3:11])/[N:4]=[C:5](/N(C)C)\[CH3:6].Cl[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(N(CC)CC)C>ClCCl>[CH3:6][C:5]1[N:4]=[C:3]([S:10][CH3:11])[NH:2][C:13](=[O:20])[C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 87308795N'-[amino(methylsulfanyl)methyl]-N,N-dimethylethanimidamide;hydroiodide

Product 1

HCID 135504073Ethyl 4-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1E)-N′-[amino(methylthio)methyl]-N,N-dimethylethanimidamide hydrogen iodide salt (73.0 g, 0.26 mole) in dry dichloromethane (900 mL), was added ethyl 3-chloro-3-oxopropanoate (44 mL, 95% Lancaster, 0.34 mole) was added under a nitrogen atmosphere. The mixture was stirred for 4 h at room temperature, cooled to 0° C. then triethylamine (107 mL, 0.78 mole) was added. The reaction mixture was stirred overnight. The solvent was removed and H2O was added. The pH was adjusted to pH=5.0 with acetic acid and extracted with ethylacetate then evaporated and crystallized from the appropriate solvent (Ethylacetate-Hexanes mixture solvent, approximately 20% ethylacetate-Hexanes). This afforded ethyl 4-methyl-2-(methylthio)-6-oxo-1,6-dihydropyrimidine-5-carboxylate (36.5 g, 62% yield) after drying under vacuum.

Workup

  1. additionwas added under a nitrogen atmosphere
  2. temperaturecooled to 0° C.
  3. stirringThe reaction mixture was stirred overnight
  4. customThe solvent was removed
  5. additionH2O was added
  6. extractionextracted with ethylacetate
  7. customthen evaporated
  8. customcrystallized from the appropriate solvent (Ethylacetate-Hexanes mixture solvent, approximately 20% ethylacetate-Hexanes)

Sources & evidence

ORD record
ord-1e3c22f6671d4c71871dfe3c5737cc46
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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