Triethylamine → N6-[1,2,3,4-tetrahydro-1-hydroxy-1-naphthalenyl]methyl adenosine

HRID 414175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414175
[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.[OH:20][C:21]1([CH2:31][NH2:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C(O)C>[OH:20][C:21]1([CH2:31][NH:32][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:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][CH2:22]1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 129148591-(Aminomethyl)-1,2,3,4-tetrahydronaphthalen-1-ol

Produkt 1

HCID 14348644N6-[1,2,3,4-tetrahydro-1-hydroxy-1-naphthalenyl]methyl adenosineAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A reaction mixture of 1.7 g of 6-chloropurine riboside, 1.7 g of (1,2,3,4-tetrahydro-1-hydroxynaphthyl)methyamine as prepared in Example B hereinafter and 2.0 g of triethylamine is refluxed in 150 ml ethanol for 24 hours. Volatiles are evaporated to dryness and residue is treated with 150 ml of cold water. Clear aqueous solution is decanted off. The water treatment is repeated twice followed by dissolving the residue in methanol and evaporating it to dryness. Co-evaporation several times with methanol affords solid material. It is dried under reduced pressure yielding 2.2 g (85%) of N6 -[1,2,3,4-tetrahydro-1-hydroxy-1-naphthalenyl]methyl adenosine having a melting point of 110°-115° C. Anals. calcd. for C21H25N5O5.0.5 C2H5OH, Found: C=58.65; H=6.26, N=15.55, C=59.27; H=6.34; N=15.53.

Aufarbeitung

  1. customVolatiles are evaporated to dryness and residue
  2. additionis treated with 150 ml of cold water
  3. customClear aqueous solution is decanted off
  4. dissolutionby dissolving the residue in methanol
  5. customevaporating it to dryness
  6. customCo-evaporation several times with methanol
  7. customaffords solid material
  8. customIt is dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b40caf6cecd745c1a682da7defadec37
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791103

Notizen zur Reaktion

Wird geladen…