Benzyl Alcohol → 2-Amino-6-Benzyloxy-9-Carboxymethylpurine

HRID 50080

Reaktionsgleichung

Reaktionsgleichung von HRID 50080
[Na].[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][C:13]([OH:15])=[O:14])=[C:5](Cl)[N:4]=1.[OH-].[Na+].[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[NH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH2:12][C:13]([OH:15])=[O:14])=[C:5]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:4]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 14798Sodium HydroxideHCID 41928332-Amino-6-chloro-9H-purine-9-acetic acidHCID 5360545Sodium

Produkt 1

HCID 100633112-Amino-6-Benzyloxy-9-Carboxymethylpurine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Sodium (2 g 87 mmol) was dissolved in benzyl alcohol (20 mL) and heated to 130° C. for 2 h. After cooling to 0° C., a solution of 2-amino-6-chloro-9-carboxymethylpurine (4.05 g, 18 mmol) in DMF (85 mL) was slowly added, and the resulting suspension stirred overnight at 20° C. Sodium hydroxide solution (1 N, 100 mL) was added and the clear solution was washed with ethyl acetate (3×100 mL). The water phase was then acidified to a pH of 3 with 4 N hydrochloric acid. The precipitate was taken up in ethyl acetate (200 mL), and the water phase was extracted with ethyl acetate (2×100 mL). The combined organic phases were washed with saturated sodium chloride solution (2×75 mL), dried with anhydrous sodium sulfate, and evaporated to dryness, in vacuo. The residue was recrystallized from ethanol (300 mL). Yield, after drying in vacuo, over sicapent: 2.76 g (52%). M.p. 159-65° C. Anal. (calc.; found): C(56.18; 55.97), H(4.38; 4.32), N(23.4; 23.10). 1H-NMR (DMSO-d6) δ: 4.82 (s, 2H); 5.51 (s, 2H); 6.45 (s, 2H); 7.45 (m, 5H); 7.82 (s, 1H).

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. washthe clear solution was washed with ethyl acetate (3×100 mL)
  3. extractionthe water phase was extracted with ethyl acetate (2×100 mL)
  4. washThe combined organic phases were washed with saturated sodium chloride solution (2×75 mL)
  5. dry with materialdried with anhydrous sodium sulfate
  6. customevaporated to dryness, in vacuo
  7. customThe residue was recrystallized from ethanol (300 mL)
  8. customYield
  9. customafter drying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1f370e4853084f438e4af38f0d02be57
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06710164B1

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