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Triethylamine → 6-Chloro-9-(2-benzoyloxyethoxymethyl)purine

HRID 614921
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 614921
[C:1]([O:9][CH2:10][CH2:11][O:12][CH2:13]Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[NH:18][CH:19]=[N:20]2.C(N(CC)CC)C.Cl.C(N(CC)CC)C>CN(C)C=O>[Cl:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH2:13][O:12][CH2:11][CH2:10][O:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 27245002-(Chloromethoxy)ethyl benzoateHCID 53592776-Chloropurine

Produkt 1

HCID 129267736-Chloro-9-(2-benzoyloxyethoxymethyl)purine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

Following substantially the procedure of Schaeffer, et al. supra but with minor modifications, 1-benzoyloxy-2-chloromethoxyethane (4.4g) was added with stirring to a dry solution of 6-chloropurine (3.1g) and triethylamine (6.5ml) in dimethylformamide (50ml). The reaction was exothermic, immediately precipitating triethylamine hydrochloride. The reaction mixture was stirred at room temperature for 24 hours and filtered. The filtrate was evaporated on a rotary evaporator at 70° C. The remaining thick amber oil was dissolved in the minimum amount of benzene and purified by column chromatography using a silica gel column. Benzene elution removed a trace of an unidentified material. Elution with ether first removed a small amount of ethylene glycol monobenzoate and then 6-chloro-9-(2-benzoyloxyethoxymethyl)purine. Recrystallization from ether gave a white material, m.p. 108.5°-111° C.

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate was evaporated on a rotary evaporator at 70° C
  3. dissolutionThe remaining thick amber oil was dissolved in the minimum amount of benzene
  4. custompurified by column chromatography
  5. washBenzene elution
  6. customremoved a trace of an unidentified material
  7. washElution with ether
  8. customfirst removed a small amount of ethylene glycol monobenzoate
  9. customRecrystallization from ether
  10. customgave a white material, m.p. 108.5°-111° C.

Quellen und Nachweise

ORD-Eintrag
ord-cea871e460ac4501952a24f5d318f434
Quelldatensatz
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04146715

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