Triethylamine → HCID 44582287, Verbindung

HRID 2036324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036324
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[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1.ClC1N=CN=C2C=1NC=N2.Cl.[OH:28][C:29]1[C:36]([OH:37])=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32].C(N(CC)CC)C>C(O)CC>[OH:28][C:29]1[C:36]([OH:37])=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][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[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 977406-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purineHCID 53592776-ChloropurineHCID 672424091194-90-7

Produkt 1

HCID 44582287HCID 44582287, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

A mixture of 10 mmol (2387 mg) 6-chloro-9-(tetrahydropyran-2-yl)purine (prepared from 10 mmol (1546 mg) of 6-chloropurine), 12 mmol (2100 mg) 2,3-dihydroxybenzylamine hydrochloride, and 7 mL of triethylamine was refluxed in n-propanol for 3 hrs. After removal of the n-propanol by vacuum evaporation, the resulting material was treated with water and extracted into ethyl acetate. The ethyl acetate solvent 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 60%, white solid. TLC (CHCl3:methanol) (4:1) (v:v): single spot; HPLC: purity>98%. 1H-NMR (300 MHz, DMSO): 1.57m (2H); 1.71 m (1H); 1.95m (2H); 2.27qq (1H, Ja=12 Hz, Jb=4.0 Hz); 3.67m (1H); 4.00d (1H, J=11.7 Hz); 4.58bs (2H); 5.63dd (1H, Ja=11.2 Hz, Jb=1.9 Hz); 6.55tt (1H, Ja=7.7 Hz, Jb=1.5 Hz); 6.63dd (1H, Ja=7.7 Hz, Jb=1.8 Hz); 6.66dd (1H, Ja=7.7 Hz, Jb=1.8 Hz); 8.24s (1H); 8.27bs (1H); 8.37s (1H), 8.96bs (1H), 9.53bs (1H). MS (ES): [M+H]+=342 (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 solvent 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. custom8.24s (1H)
  10. custom8.37s (1H), 8.96bs (1H), 9.53bs (1H)

Quellen und Nachweise

ORD-Eintrag
ord-92b692b8cf684fc69f80e9a1e4aa01a7
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575182B2

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