4-Fluorobenzyl chloride → 6-Amino-2-chloro-9-(4-fluorobenzyl)purine

HRID 2269146

Reaktionsgleichung

Reaktionsgleichung von HRID 2269146
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:23][C:22]1[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=1

Komponenten

5

Edukt 3

HCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 949042-Chloroadenine

Produkt 1

HCID 115146366-Amino-2-chloro-9-(4-fluorobenzyl)purineAusbeute 1.970,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Amino-2-chloropurine (5.02 g) and potassium carbonate (5 g, 36 mmol) were suspended in DMF (200 ml) and thereto was added 4-fluorobenzyl chloride (5 ml, 42 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo to dryness, and to the residue was added water. The mixture was extracted with chloroform and the organic layer was washed with water, dried on sodium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (162 g).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. additionto the residue was added water
  3. extractionThe mixture was extracted with chloroform
  4. washthe organic layer was washed with water
  5. customdried on sodium sulfate
  6. concentrationconcentrated in vacuo to dryness
  7. customThe residue was purified with silica gel chromatography (2% methanol/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-de60888fa9cc4327bb7238ebcbcc63fe
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329381B1

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