Potassium Carbonate → 2-Chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine

HRID 1010973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1010973
[Cl:1][C:2]1[NH:3][C:4]([NH2:11])=[C:5]2[C:9]([N:10]=1)=[N:8][CH:7]=[N:6]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CN(C=O)C.C(Cl)(Cl)Cl.C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:19][CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:4]([NH2:11])[N:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 178509092HCID 178509092, Verbindung

Produkt 1

HCID 576998042-Chloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amineAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21906603Chloroform isopropyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of 2-chloro-1H-purin-6-amine (1.57 g) and potassium carbonate (2.57 g) in DMF (55 mL) was added 4-(bromomethyl)tetrahydro-2H-pyran (2.0 g) in one portion. The mixture was stirred at 90° C. overnight. The reaction mixture was taken up in chloroform/isopropanol (3:1, 100 mL) and was extracted with water (100 mL). The organics were separated and the aqueous was extracted with chloroform/isopropanol (3:1, 2×50 mL). The organics were combined, dried by passing through a hydrophobic frit and concentrated in vacuo to give the title compound as an off-white solid (1.30 g, 52%).

Aufarbeitung

  1. extractionwas extracted with water (100 mL)
  2. customThe organics were separated
  3. extractionthe aqueous was extracted with chloroform/isopropanol (3:1, 2×50 mL)
  4. customdried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8e864a1a70e4697a29ffd96127b4490
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977344B2

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