Sodium hydride → 4-chloro-5-iodo-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 51482

Reaktionsgleichung

Reaktionsgleichung von HRID 51482
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[H-].[Na+].[H][H].S(O[CH:27]1[CH2:31][CH2:30][O:29][CH2:28]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:27]3[CH2:31][CH2:30][O:29][CH2:28]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 227364154-chloro-5-iodo-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (5.0 g) was added to a mixture of sodium hydride (0.79 g of a 60% dispersion in mineral oil) in dimethylformamide (100 ml) with stirring under nitrogen at 0° C. The mixture was stirred until hydrogen evolution ceased. 3-Tosyloxytetrahydrofuran (4.65 g) was added at 0° C. and then the mixture was warmed to 90° C. The mixture was stirred at this temperature for 2 hours and then overnight at ambient temperature. Water (100 ml) was added cautiously and the mixture was extracted with ethyl acetate to give 4-chloro-5-iodo-7-(3-tetrahydrofuryl)-7H-pyrrolo[2,3-d]pyrimidine, m.p. 184-186° C.

Aufarbeitung

  1. temperaturethe mixture was warmed to 90° C
  2. stirringThe mixture was stirred at this temperature for 2 hours
  3. customovernight
  4. customat ambient temperature
  5. extractionthe mixture was extracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-42cab23401b141169cdb7e9ba9557641
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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