Triphenylphosphine → 9-[2-(Diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurine

HRID 1031070

Reaktionsgleichung

Reaktionsgleichung von HRID 1031070
[OH:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21].[CH2:22]([O:24][P:25]([CH2:30][S:31][CH2:32][CH2:33]O)(=[O:29])[O:26][CH2:27][CH3:28])[CH3:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH2:22]([O:24][P:25]([CH2:30][S:31][CH2:32][CH2:33][O:1][N:2]1[CH:10]=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:11]1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21])([O:26][CH2:27][CH3:28])=[O:29])[CH3:23]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10376467HCID 10376467, VerbindungHCID 145239709-Hydroxy-6-phthalimidopurine

Produkt 1

HCID 198195589-[2-(Diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurineAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 9-hydroxy-6-phthalimidopurine (0.5 g, 2.2 mmol). diethyl-2-hydroxyethylthiomethylphosphonate (0.45 g. 2 mmol) and triphenylphosphine (0.52 g, 2 mmol) was dissolved in dry tetrahydrofuran (20 ml) and cooled to 0°-5° C. A solution of diethylazodicarboxylate (0.348 g, 2.0 mmol) in dry tetrahydrofuran (10 ml) was added dropwise with stirring, and after the addition was completed the reaction was stirred at room temperature for 18 hours. The solvent was then removed in vacuo, and the residue was purified by column chromatography on silica using ethyl acetate: methanol (98:2) as eluent to give 9-[2-(diethoxyphosphorylmethylthio)ethoxy]-6-phthalimidopurine (0.45 g 56%) as a white solid after crystallisation from acetone/diethyl ether, m.p. 115°-116° C.; γmax (EtOH) 271mm (s 14020) υmax (KBr) 3100, 3060, 2960, 2900, 1780, 1725, 1650, 1600, 1580, 1453, 1400, 1380, 1360, 1320, 1280, 1240, and 1200 cm-1 ; δH [(CD3)2SO] 1.25 (6H, t, J 7Hz 2 × CH3), 3.0 (2H, d, J 13Hz, PCH2S), 3.1 (2H, t, J 7Hz CH20, 4.0 (4H, m, 2 × CH2), 4.7 (2H, t, J 7Hz, CH2S), 8.1 (4H, m, Ar H), 9.0 (1H, s, 2H), 9.1 (1H, s, 8-H). (Found C, 48.65; H, 4.55; N, 14.23%. C20H22N5O6PS requires C,48.87; H, 4.51; N, 14.25%).

Aufarbeitung

  1. temperaturecooled to 0°-5° C
  2. additionafter the addition
  3. stirringwas stirred at room temperature for 18 hours
  4. customThe solvent was then removed in vacuo
  5. customthe residue was purified by column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-404cbf1e8bf24a3e8bc3b8b66d880dab
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05108994

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