Bromocyclopentane → HCID 11774121, Verbindung

HRID 1984211Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984211
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[N:21]=[C:20]([Cl:22])[N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][NH:17]2.Br[CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13]1[N:21]=[C:20]([Cl:22])[N:19]=[C:18]2[C:14]=1[N:15]=[CH:16][N:17]2[CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

5

Edukt 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 178478467[2-(3-Chloro-propoxy)-phenyl]-(2-chloro-9H-purin-6-yl)-amine

Produkt 1

HCID 11774121HCID 11774121, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

[2-(3-Chloro-propoxy)-phenyl]-(2-chloro-9H-purin-6-yl)-amine (3 mmol), bromo-cyclopentane (4.1 mmol) and potassium carbonate (water free, 3.6 mmol) are suspended in DMF (20 ml) and heated up to 50° C. and the mixture is stirred at this temperature for 5 hours. After cooling to RT the mixture is poured on water and extracted 3 times with ethyl acetate. The combined organic phases are washed twice with brine and the extract is dried over sodium sulfate and evaporated. The residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=20:1) as mobile phase. The product containing fractions are combined and evaporated. The product is cristallized from diethyl ether/pentane, filtered off and dried. A solid powder with mp. 110-112° C., Rf=0.78 (CH2Cl2/MeOH=20:1) is obtained.

Aufarbeitung

  1. temperatureAfter cooling to RT the mixture
  2. additionis poured on water
  3. extractionextracted 3 times with ethyl acetate
  4. washThe combined organic phases are washed twice with brine
  5. dry with materialthe extract is dried over sodium sulfate
  6. customevaporated
  7. customThe residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=20:1) as mobile phase
  8. additionThe product containing fractions
  9. customevaporated
  10. filtrationfiltered off
  11. customdried
  12. customA solid powder with mp. 110-112° C., Rf=0.78 (CH2Cl2/MeOH=20:1) is obtained

Quellen und Nachweise

ORD-Eintrag
ord-f9f321cbf4c04453a1735ec03f8cbc64
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544688B2

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