Diethyl Ether → 2-Amino-9-(2-formyloxyethoxymethyl)adenine

HRID 2285568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2285568
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][OH:15])=[C:4]([NH2:16])[N:3]=1.C[CH2:18][O:19]CC>C(O)=O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][O:15][CH:18]=[O:19])=[C:4]([NH2:16])[N:3]=1

Komponenten

4

Edukt 2

HCID 3283Diethyl EtherHCID 945882,6-Diamino-9-(2-hydroxyethoxymethyl)purine

Produkt 1

HCID 132555722-Amino-9-(2-formyloxyethoxymethyl)adenine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A solution of 2-amino-9-(2-hydroxyethoxymethyl)adenine (0.5 g) in 97% formic acid (2.5 ml) was stirred in an ice bath for 3 hours, and then at room temperature overnight. Dry ether (80 ml) was added and the mixture chilled. The solid was removed by filtration and dissolved in hot acetonitrile (125 ml); residual solids were removed by filtration. The filtrate was applied to a column containing silica gel (14 g) in acetonitrile. The column was eluted with dry acetone. The eluate was evaporated and the residual solid recrystallized from acetonitrile to give 2-amino-9-(2-formyloxyethoxymethyl)adenine (93 mg, m.p. 238°-240° C.).

Aufarbeitung

  1. customat room temperature
  2. customovernight
  3. temperaturethe mixture chilled
  4. customThe solid was removed by filtration
  5. dissolutiondissolved in hot acetonitrile (125 ml)
  6. customresidual solids were removed by filtration
  7. additioncontaining silica gel (14 g) in acetonitrile
  8. washThe column was eluted with dry acetone
  9. customThe eluate was evaporated
  10. customthe residual solid recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-2e9471e96f7e4f93ba2feec33c32f9bb
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04323573

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