Dimethylformamide dimethyl acetal → (E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylate

HRID 41479

Reaktionsgleichung

Reaktionsgleichung von HRID 41479
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:14])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH3:15][N:16]([CH:18](OC)OC)[CH3:17]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](/[CH:14]=[CH:15]/[N:16]([CH3:18])[CH3:17])=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 188208Ethyl-2-methylthio-4-methyl-5-pyrimidine carboxylate

Produkt 1

HCID 86657908(E)-ethyl 4-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Methyl-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester 3 (18.0 g, 84.8 mmol) was dissolved in DMF (50 mL), N,N-Dimethylformamidedimethylacetal (22.5 mL, 170 mmol) and stirred at reflux for 3 hours. Then mixture was concentrated, the residue was dissolved in TCM, washed with water, dried, filtered, and concentrated. The product was purified by crystallization from ether to yield in a colorless solid (14.0 g, 52.5 mmol, 62%).

Aufarbeitung

  1. temperatureat reflux for 3 hours
  2. concentrationThen mixture was concentrated
  3. dissolutionthe residue was dissolved in TCM
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was purified by crystallization from ether

Quellen und Nachweise

ORD-Eintrag
ord-dc974b9b448b4f40ae01977f5f513159
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530650B2

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