Sodium hydride → 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1904110

Reaktionsgleichung

Reaktionsgleichung von HRID 1904110
[H-].[Na+].[Cl:3][C:4]1[C:5]2[CH:14]=[CH:13][NH:12][C:6]=2[N:7]=[C:8]([S:10][CH3:11])[N:9]=1.[CH2:15]([O:22][C@H:23]1[C@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:26]([CH2:36][O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:25][C@@H:24]1Cl)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[Cl:3][C:4]1[C:5]2[CH:14]=[CH:13][N:12]([C@@H:24]3[O:25][C@H:26]([CH2:36][O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@@H:27]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C@@H:23]3[O:22][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]=2[N:7]=[C:8]([S:10][CH3:11])[N:9]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 53244144-chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidineHCID 10895454(2R,3R,4S,5R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-chlorotetrahydrofuran

Produkt 1

HCID 132771774-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A suspension of 3.1 g sodium hydride, 25.9 g of 4-chloro-2-methylmercapto-7H-pyrrolo[2,3-d]pyrimidine, and 250 ml of dry dimethylformamide (DMF) is stirred at 50° C. for 0.5 hour, cooled, and added to 62.8 g of 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride. The solution is stirred at ambient temperature for 15 hours, concentrated in vacuo, and distributed between a mixture of ethyl acetate and water. Chromatography of the dried (MgSO4) layer over silica gel with 4:1 toluene-ethyl acetate provides 76 g of yellow, syrupy 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine.

Aufarbeitung

  1. temperaturecooled
  2. stirringThe solution is stirred at ambient temperature for 15 hours
  3. concentrationconcentrated in vacuo
  4. additiondistributed between a mixture of ethyl acetate and water
  5. dry with materialChromatography of the dried (MgSO4) layer over silica gel with 4:1 toluene-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f2a5eca74f644fa99da0b3eeff497609
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04439604

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