Triethylamine → 8-(4-Bromobenzylamino)adenosine

HRID 1713259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713259
Br[C:2]1[N:3]([C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=2[N:19]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6].Cl.[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1.C(N(CC)CC)C>C(O)C>[Br:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH:28][C:2]2[N:3]([C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=3[N:19]=2)[C@@H:4]2[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]2[OH:6])=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 965448-BromoadenosineHCID 27240964-Bromobenzylamine hydrochloride

Produkt 1

HCID 674555318-(4-Bromobenzylamino)adenosineAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 8-bromoadenosine (0.100 g), 4-bromobenzylamine hydrochloride (0.193 g) and triethylamine (0.201 mL) in ethanol (2.9 mL) was stirred under reflux for 96 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.118 g).

Aufarbeitung

  1. temperatureunder reflux for 96 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography on aminopropylated silica gel (eluent: dichloromethane/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-639b01dafef94996920f61aa46db08fb
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795236B2

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