Dimethylformamide → N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-9-(2-pyridinylmethyl)-9H-purin-8-amine

HRID 2248814

Reaktionsgleichung

Reaktionsgleichung von HRID 2248814
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[NH:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]2[N:20]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=3)[C:21]3[C:26]([N:27]=2)=[CH:25][N:24]=[CH:23][N:22]=3)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][N:12]2[CH2:13][CH2:14][CH:15]([NH:18][C:19]3[N:20]([CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[C:21]4[C:26]([N:27]=3)=[CH:25][N:24]=[CH:23][N:22]=4)[CH2:16][CH2:17]2)=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 875134-(2-Chloroethyl)phenyl methyl etherHCID 19785321N-(4-piperidinyl)-9-(2-pyridinylmethyl)-9H-purin-8-amine

Produkt 1

HCID 19785338N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-9-(2-pyridinylmethyl)-9H-purin-8-amineAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2 parts of 1-(2-chloroethyl)-4-methoxybenzene, 3.1 parts of N-(4-piperidinyl)-9-(2-pyridinylmethyl)-9H-purin-8-amine, 1.5 parts of sodium carbonate and 45 parts of N,N-dimethylformamide was stirred overnight at 70° C. The reaction mixture was poured into water. The product was extracted with dichloromethane. 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 2.2 parts (50%) of N-[1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]-9-(2-pyridinylmethyl)-9H-purin-8-amine; mp. 144.5° C. (compound 74).

Aufarbeitung

  1. extractionThe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated
  9. customThe residue was crystallized from acetonitrile
  10. filtrationThe product was filtered off
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c246b5b1ac6c4ad7ad3ecbf07349e6aa
Quelldatensatz
uspto-grants-1991_08
Patentnummer
US05041448

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