Adenine → 9-[(Diethylphosphonomethoxy)methoxymethyl]adenine

HRID 1553

Reaktionsgleichung

Reaktionsgleichung von HRID 1553
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.Cl[CH2:14][O:15][CH2:16][O:17][CH2:18][P:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22].C([O:28]P([O-])(OCC)=O)C.ClCOCOCCl>CN(C=O)C>[CH2:21]([O:20][P:19]([CH2:18][O:17][CH2:16][O:15][CH2:14][N:7]1[CH:8]=[N:9][C:10]2[C:6]1=[N:5][CH:4]=[N:3][C:11]=2[NH2:12])([O:23][CH2:24][CH3:25])=[O:28])[CH3:22]

Komponenten

7

Edukt 5

HCID 190AdenineHCID 24758Sodium hydrideHCID 5166299Diethyl phosphoric acidHCID 14843538Bis(chloromethoxy)methaneHCID 57012807Chloromethoxy(diethoxyphosphinomethoxy)methane

Produkt 1

HCID 148435419-[(Diethylphosphonomethoxy)methoxymethyl]adenine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 60% sodium hydride in mineral oil (1.4 g, 34.5 mmol) in DMF (100 mL) was added adenine (4.7 g, 34.5 mmol) and the mixture was stirred at 80° C. for 1 hr. To the resulting yellow solution was added dropwise a solution of chloromethoxy(diethoxyphosphinomethoxy)methane [(prepared from diethylphosphate (4.4 mL, 34.5 mmol) and bis(chloromethoxy)methane (25 g, 172 mmol)] in DMF (20 mL) under nitrogen. After stirring at 25° C. for 15 hr, volatiles were removed in vacuo, and the resulting oily residue was purified by silica gel column chromatography using CH2Cl2 /10% MeOH as eluent to obtain the title compound as a colorless oil: yield 6.0 g (50%).

Aufarbeitung

  1. stirringAfter stirring at 25° C. for 15 hr
  2. customvolatiles were removed in vacuo
  3. customthe resulting oily residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-93d03e24b2e64b579f6821175b3c99c2
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726174

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