Acetone → HCID 178458928, Verbindung

HRID 1692661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692661
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2C2CCCCO2)=[C:4]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1.[Li]CCCC.[CH3:28][C:29]([CH3:31])=[O:30]>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([C:29]([OH:30])([CH3:31])[CH3:28])[NH:8]2)=[C:4]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[N:3]=1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 134629464-(2-Chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)morpholineHCID 178418339Butyllithium

Produkt 1

HCID 178458928HCID 178458928, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

4-(2-Chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)morpholine (2.76 gm) was cooled in THF to −78° C. A 2.5 M solution of n-BuLi in THF (1.5 eq) was added dropwise over 20 minutes. The reaction was stirred at −78° C. for 30 mins, after which acetone (1.56 mL) was added and the reaction was stirred over 2 hours, slowly warming to 0° C. The reaction mixture was then quenched with water and extracted with ethyl acetate. The crude product 2-(2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)propan-2-ol was concentrated and brought up in MeOH. The THP group was then removed via General Procedure D. The reaction mixture was concentrated and the crude solid was brought up in water, filtered and collected and dried overnight to give 2.23 gm of 2-(2-chloro-6-morpholino-9H-purin-8-yl)propan-2-ol as a light yellow solid.

Aufarbeitung

  1. stirringthe reaction was stirred over 2 hours
  2. temperatureslowly warming to 0° C
  3. customThe reaction mixture was then quenched with water
  4. extractionextracted with ethyl acetate
  5. concentrationThe crude product 2-(2-chloro-6-morpholino-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-8-yl)propan-2-ol was concentrated
  6. customThe THP group was then removed via General Procedure D
  7. concentrationThe reaction mixture was concentrated
  8. filtrationfiltered
  9. customcollected
  10. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-90831f64a7c7409aa80fe788edf29292
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158624B2

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