1-Bromo-1-propene → 9-[(4-fluorophenyl)methyl]-N-[1-(2-propenyl)-4-piperidinyl)-9H-purin-8-amine

HRID 256664

Reaktionsgleichung

Reaktionsgleichung von HRID 256664
Br[CH:2]=[CH:3][CH3:4].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:21]([NH:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][CH:18]=3)=[CH:8][CH:7]=1.C(=O)([O-])O.[Na+]>C(O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:21]([NH:22][CH:23]3[CH2:24][CH2:25][N:26]([CH2:4][CH:3]=[CH2:2])[CH2:27][CH2:28]3)=[N:20][C:19]3[C:14]2=[N:15][CH:16]=[N:17][CH:18]=3)=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 115331-Bromo-1-propeneHCID 516892Sodium BicarbonateHCID 197853439-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-9H-purin-8-amine

Produkt 1

HCID 197852429-[(4-fluorophenyl)methyl]-N-[1-(2-propenyl)-4-piperidinyl)-9H-purin-8-amineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 1.2 parts of bromo-1-propene, 3.26 parts of 9-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-9H-purin-8-amine, 1.5 parts of sodium hydrogen carbonate and 40 parts of ethanol was stirred for 1 hour at reflux temperature. The reaction mixture was filtered over diatomaceous earth while hot and the filtrate was evaporated. The residue was taken up in water and the product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 0.8 parts (22%) of 9-[(4-fluorophenyl)methyl]-N-[1-(2-propenyl)-4-piperidinyl)-9H-purin-8-amine; mp. 144.8° C. (compound 120).

Aufarbeitung

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered over diatomaceous earth while hot and the filtrate
  3. customwas evaporated
  4. extractionthe product was extracted with 4-methyl-2-pentanone
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from acetonitrile
  13. filtrationThe product was filtered off
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6a068b16c7e5448499de677d54ff443f
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05258380

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