Diisopropylethylamine → 6-(4-Hydroxybenzylamino)-9-(tetrahydrofuran-2-yl)-purine

HRID 2422329

Reaktionsgleichung

Reaktionsgleichung von HRID 2422329
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[CH2:15][CH2:14][CH2:13][O:12]1.ClC1N=CN=C2C=1NC=N2.[OH:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH2:32])=[CH:29][CH:28]=1.C(N(C(C)C)C(C)C)C>C(O)CC>[OH:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][NH:32][C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)=[CH:29][CH:28]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 974724-HydroxybenzylamineHCID 2394846-chloro-9-(tetrahydrofuran-2-yl)-9H-purineHCID 53592776-Chloropurine

Produkt 1

HCID 445821556-(4-Hydroxybenzylamino)-9-(tetrahydrofuran-2-yl)-purineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

A mixture of 10 mmol (2240 mg) of 6-chloro-9-(tetrahydrofuran-2-yl)purine (prepared from 10 mmol (1546 mg) of 6-chloropurine), 12 mmol (1478 mg) of 4-hydroxybenzylamine, and 5 ml of N-ethyldiisopropylamine was refluxed in n-propanol for 3 hours. After removal of the n-propanol by vacuum evaporation, the resulting material was treated with water and extracted into ethyl acetate. The ethyl acetate phase was evaporated and the residuum subsequently washed with 30 ml of petroleum ether. The solid residue was filtered off and the crude product crystallized from methanol. Yield 80%, white solid. TLC (EtOAc:hexane (1:1 (v:v)): single spot; HPLC: purity >98%. 1H NMR (400 MHZ, DMSO): 1.36tt (2H, Ja=7.8 Hz, Jb=2.2 Hz); 2.23m (1H); 2.32m (1H); 3.62dd (1H, Ja=10.8 Hz, Jb=3.8 Hz); 3.87dd (1H, Ja=10.8 Hz, Jb=3.8 Hz); 4.62s (2H); 6.23dd (1H, Ja=5.3 Hz, Jb=1.5 Hz); 6.71d (2H, J=8.3 Hz); 7.21d (2H, J=8.3 Hz); 8.06bs (1); 8.16s (1H); 8.28s (1H); 9.23s (1H). MS (ES): [M+H]+=312 (100).

Aufarbeitung

  1. customAfter removal of the n-propanol
  2. customby vacuum evaporation
  3. additionthe resulting material was treated with water
  4. extractionextracted into ethyl acetate
  5. customThe ethyl acetate phase was evaporated
  6. washthe residuum subsequently washed with 30 ml of petroleum ether
  7. filtrationThe solid residue was filtered off
  8. customthe crude product crystallized from methanol
  9. custom4.62s (2H)
  10. custom8.16s (1H)
  11. custom8.28s (1H)
  12. custom9.23s (1H)

Quellen und Nachweise

ORD-Eintrag
ord-65158dbfa19c4c87beb4fef7ccef0a99
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960397B2

Verknüpfte Notizen

Wird geladen…