Triethylamine → N6-[2,3-dihydro-1H-inden-1-yl]methyl-adenosine

HRID 414173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414173
[CH:1]1[N:6]=[C:5](Cl)[C:4]2[N:8]=[CH:9][N:10]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]3[OH:19])[C:3]=2[N:2]=1.[CH:20]1([CH2:29][NH2:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1.C(N(CC)CC)C>C(O)C>[CH:20]1([CH2:29][NH:30][C:5]2[C:4]3[N:8]=[CH:9][N:10]([C:3]=3[N:2]=[CH:1][N:6]=2)[C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2[OH:19])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 143486922,3-dihydro-1H-inden-1-ylmethanamine

Produkt 1

HCID 14348694N6-[2,3-dihydro-1H-inden-1-yl]methyl-adenosineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3.0 g of 6-chloropurine riboside, 2.0 g of 1-indanylmethylamine as prepared in Example A hereinafter and 3.18 g of triethylamine are refluxed in 75 ml of absolute ethanol under nitrogen for 24 hours. The reaction is cooled to room temperature, precipitated nucleoside is filtered, washed with ethanol and dried affording 2.78 g (67%) of N6 -[2,3-dihydro-1H-inden-1-yl]methyl-adenosine having a melting point of 137°-139° C. Anals. calcd. for C20H23N5O4 ; Found: C=60.44; H=5.83; N=17.62 C=60.81; H=5.70; N=17.35.

Aufarbeitung

  1. customprecipitated nucleoside
  2. filtrationis filtered
  3. washwashed with ethanol
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8db04e701b1f4b928df61376ff2c8c63
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791103

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