Adenine → 2-(6-Aminopurin-9-yl)ethanol

HRID 336057

Reaktionsgleichung

Reaktionsgleichung von HRID 336057
[H-].[Na+].[N:3]1[C:11]([NH2:12])=[C:10]2[C:6]([N:7]=[CH:8][NH:9]2)=[N:5][CH:4]=1.Br[CH2:14][CH2:15][O:16]C(=O)C1C=CC=CC=1.N>CN(C=O)C.CO>[OH:16][CH2:15][CH2:14][N:7]1[CH:8]=[N:9][C:10]2[C:6]1=[N:5][CH:4]=[N:3][C:11]=2[NH2:12]

Komponenten

7

Edukt 4

HCID 190AdenineHCID 222AmmoniaHCID 24758Sodium hydrideHCID 5230902-Bromoethyl Benzoate

Produkt 1

HCID 2426522-(6-Aminopurin-9-yl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of 60% NaH in mineral oil (1.70 g, 42.57 mmol) in anhydrous DMF (120 mL) was added adenine (5.23 g, 38.70 mmol) under argon, and the mixture was heated at 60° C. for 1 h. 2-Bromoethylbenzoate (9.2 mL, 58.06 mmol) was added dropwise at 60° C., and the reaction was stirred at this temperature for 16 h. The mixture was then filtered to remove insoluble materiel, the filtrate was evaporated under reduced pressure and co-evaporated three times with toluene. The residue was triturated with EtOAc then filtered to give a white solid, which was immediately resuspended in a saturated ammonia solution in MeOH (400 mL). The reaction mixture was stirred for 14 h at room temperature, and then methanol was removed under reduced pressure. Recrystallization from EtOH afforded compound 2 (5.87 g, 85%): mp 236° C. (Lit. 238-239° C.); 1H NMR (DMSO-d6): 8.13 (s, 1H, H-2), 8.10 (s, 1H, H-8), 7.23 (bs, 2H, NH2), 5.05 (bs, 1H, OH), 4.19 (t, J=5.2 Hz, 2H, CH2O), 3.71 (t, J=5.2 Hz, 2H, CH2N). 13C NMR (DMSO-d6) δ: 155.79, 152.23, 149.44, 141.46, 118.55, 59.17, 45.61. MS (GT, FAB+): 136 (B+1H)+, 180 (M+1H)+, 202 (M+Na)+.

Aufarbeitung

  1. filtrationThe mixture was then filtered
  2. customto remove insoluble materiel
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was triturated with EtOAc
  5. filtrationthen filtered
  6. customto give a white solid, which
  7. stirringThe reaction mixture was stirred for 14 h at room temperature
  8. custommethanol was removed under reduced pressure
  9. customRecrystallization from EtOH afforded compound 2 (5.87 g, 85%)
  10. custommp 236° C. (Lit. 238-239° C.)

Quellen und Nachweise

ORD-Eintrag
ord-91dc02665b9c4ab98a90a2ab37b24071
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884011B2

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