Sodium Carbonate → 1,7-dimethyl-1H,5H-imidazo[1,2 a]pyrimidin-5-one (E)-2-butenedioate

HRID 1708922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1708922
ClCC[C:4]1[C:9](=[O:10])[N:8]2[CH:11]=[CH:12][N:13]([CH3:14])[C:7]2=[N:6][C:5]=1[CH3:15].C([O:18]CCN1C2=NC=CC=C2N=C1CN1CCNCC1)C.[C:37](=[O:40])([O-:39])[O-].[Na+].[Na+]>CC(C)CC(=O)C>[C:9]([OH:10])(=[O:18])/[CH:4]=[CH:5]/[C:37]([OH:39])=[O:40].[CH3:14][N:13]1[C:7]2=[N:6][C:5]([CH3:15])=[CH:4][C:9](=[O:10])[N:8]2[CH:11]=[CH:12]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 19100910HCID 19100910, VerbindungHCID 19911564HCID 19911564, Verbindung

Produkt 1

HCID 1317164981,7-dimethyl-1H,5H-imidazo[1,2 a]pyrimidin-5-one (E)-2-butenedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 2.7 parts of 6-(2-chloroethyl)-1,7-dimethyl-1H,5H-imidazo[1,2-a]pyrimidin-5-one, 2.9 parts of 3-(2-ethoxyethyl)-2-(1-piperazinylmethyl)-3H-imidazo[4,5-b]pyridine, 1.06 parts of sodium carbonate and 80 parts of 4-methyl-2-pentanone was stirred first for 44 hours at reflux temperature and then over weekend at room temperature. The reaction mixture was evaporated and the residue was taken up in water. The product was extracted with dichloromethane. The extracted was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)2-butenedioate salt in 2-propanol. The salt was filtered off and dried, yielding 3.36 parts (47.3%) of 6-[2-[4-[3-(3-ethoxyethyl)-3H-imidazo[4,5-b]-pyridin-2-yl]methyl]1-piperazinyl]ethyl]1,7-dimethyl-1H,5H-imidazo[1,2 a]pyrimidin-5-one (E)-2-butenedioate(1:2); mp. 162.5° C. (compound 81).

Aufarbeitung

  1. temperatureat reflux temperature
  2. waitover weekend at room temperature
  3. customThe reaction mixture was evaporated
  4. extractionThe product was extracted with dichloromethane
  5. washThe extracted was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated
  13. filtrationThe salt was filtered off
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a8620093ec044c35b797bd13616e956a
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04946843

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