Acetone → 9-[(4-fluorophenyl)methyl]-N-[1-(1-methylethyl)-4-piperidinyl]-9H-purin-8-amine

HRID 2248819

Reaktionsgleichung

Reaktionsgleichung von HRID 2248819
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]([NH:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][CH:14]=3)=[CH:4][CH:3]=1.S1C=[CH:28][CH:27]=[CH:26]1.CC(=O)C.[H][H]>CO.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]([NH:18][CH:19]3[CH2:20][CH2:21][N:22]([CH:27]([CH3:28])[CH3:26])[CH2:23][CH2:24]3)=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][CH:14]=3)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 8030ThiopheneHCID 197853439-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-9H-purin-8-amineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 197853089-[(4-fluorophenyl)methyl]-N-[1-(1-methylethyl)-4-piperidinyl]-9H-purin-8-amineAusbeute 27,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A mixture of 4.9 parts of 9-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-9H-purin-8-amine, 1 part of a solution of thiophene in methanol 4%, 120 parts off methanol and 8 parts of 2-propanone was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was 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 crystallized from acetonitrile, yielding 1.5 parts (27.2%) of 9-[(4-fluorophenyl)methyl]-N-[1-(1-methylethyl)-4-piperidinyl]-9H-purin-8-amine; mp. 185.6° C. (compound 138).

Aufarbeitung

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-5a48fa4d98324b7da6e9b6145aec16e8
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05041448

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