Ethylamine → 2-(Benzyloxy)-N-ethyladenosine

HRID 966390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 966390
[H][H].[CH2:3]([NH2:5])[CH3:4].[CH2:6]([O:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[C@@H:23]2[O:35][C@H:34]([CH2:36][O:37]C(=O)C)[C@@H:29]([O:30]C(=O)C)[C@H:24]2[O:25]C(=O)C)=[C:16](Cl)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH2:6]([O:13][C:14]1[N:15]=[C:16]([NH:5][CH2:3][CH3:4])[C:17]2[N:18]=[CH:19][N:20]([C:21]=2[N:22]=1)[C@@H:23]1[O:35][C@H:34]([CH2:36][OH:37])[C@@H:29]([OH:30])[C@H:24]1[OH:25])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

4

Edukt 3

HCID 6341EthylamineHCID 59107260HCID 59107260, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 591072552-(Benzyloxy)-N-ethyladenosineAusbeute 40 %

Versuchsvorschrift

A compound having a structure of the above formula was prepared where the substituent R1 is —CH2CH3, R2 is hydrogen, and R3 is benzyl (—CH2C6H5). The compound (C19H23N5O5) was prepared by reaction of ethylamine with 2-benzyloxy-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (Example 3) as described in Example 2, Step E. The final product was isolated in 40% yield as a solid with melting point of 170-171° C. 1H-NMR (DMSO-d6): δ 1.13 (t, 3H, J=8); 3.6 (m, 4H); 3.9 (m, 1H); 4.1 (m, 1H); 4.5 (m, 1H); 5.18 (m, 2H); 5.32 (s, 2H); 5.42 (d, 1H, J×6); 5.78 (d, 1H, J=6); 7.41 (m, 5H); 7.93 (bm, 1H); 8.15 (s, 1H).

Aufarbeitung

  1. customwas prepared where the substituent R1

Quellen und Nachweise

ORD-Eintrag
ord-b9a31fe0fef34ecf9c1c131d437dde49
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951932B2

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