2,6-Dichloropurine → 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-beta-D-ribofuranosyl)-purine

HRID 1082098

Reaktionsgleichung

Reaktionsgleichung von HRID 1082098
[CH3:1][O:2][CH2:3][C@H:4]1[O:12][CH:7](OC(=O)C)[C@H:6]([O:13][C:14](=[O:16])[CH3:15])[C@@H:5]1[O:17][C:18](=[O:20])[CH3:19].[Cl:21][C:22]1[N:30]=[C:29]2[C:25]([NH:26][CH:27]=[N:28]2)=[C:24]([Cl:31])[N:23]=1>C(Cl)(Cl)Cl>[C:14]([O:13][C@@H:6]1[C@H:5]([O:17][C:18](=[O:20])[CH3:19])[C@@H:4]([CH2:3][O:2][CH3:1])[O:12][C@H:7]1[N:28]1[CH:27]=[N:26][C:25]2[C:29]1=[N:30][C:22]([Cl:21])=[N:23][C:24]=2[Cl:31])(=[O:16])[CH3:15]

Komponenten

4

Edukt 2

HCID 53244122,6-DichloropurineHCID 153833205-O-Methyl-1,2,3-tri-O-acetyl-D-ribofuranose

Produkt 1

HCID 110698082,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-beta-D-ribofuranosyl)-purineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

5-O-Methyl-1,2,3-tri-O-acetyl-D-ribofuranose (5.0 g, 17 mmol) and 2,6-dichloropurine (3.3 g, 17 mmol) were thoroughly mixed. A catalytic amount of p-toluene sulfuric acid (50 mg) was added and the reaction mixture was heated to 140° C. at which point a homogeneous melt was obtained. The fusion was continued at 140° C. under oil pump vacuum for 0.5 h. The reaction mixture was dissolved in chloroform (200 ml) and washed with aqueous sodium bicarbonate (3×50 ml) and water (2×50 ml). The organic phase was dried (MgSO4), evaporated in vacuo and purified by flash chromatography eluting with a mixture of n-heptane and ethyl acetate (1:1) to provide 9-(2',3'-di-O-acetyl-5'-O-methyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (1.0 g, 14%) as an oil which crystallized from diethyl ether. A mixture of α/β-anomers (1.2 g, 17%) was also isolated, with mp 59°-61° C. 1H-NMR (400 MHz,CDCL3) δ2.06 (3H, s, --OCOCH3), 3.49 (3H, s, OCH3), 3.67, 3.72 (2H, ABX, H-5'a and H-5'b), 4.39 (1H, d, H-4'), 5.58 (1H, d, H-3'), 5.75 (1H, t, H-2'), 6.38 (1H, d, H-1'), 8.56 (1H, s, H-8). C15H16Cl2N4O6 requires C, 43.0; H, 3.9; N, 13.4. Found C, 43.1, H, 3.9, N, 13.2%.

Aufarbeitung

  1. customwas obtained
  2. washwashed with aqueous sodium bicarbonate (3×50 ml) and water (2×50 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated in vacuo
  5. custompurified by flash chromatography
  6. washeluting with a mixture of n-heptane and ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-bb08e02bd3dd4a82b03421ca20827680
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589467

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