Iodine → 6-Chloro-2-iodo-9-isopropyl-9H-purine

HRID 1241344Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241344
[Cl:1][C:2]1[N:10]=[C:9](N)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13].II.N(OCCC(C)C)=O.C(I)[I:26]>C1COCC1.[Cu]I>[Cl:1][C:2]1[N:10]=[C:9]([I:26])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]([CH3:14])[CH3:13]

Komponenten

7

Edukt 4

HCID 807IodineHCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 219337716-Chloro-9-isopropyl-9h-purin-2-amine

Produkt 1

HCID 65389046-Chloro-2-iodo-9-isopropyl-9H-purineAusbeute 324,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6-Chloro-9-isopropyl-9H-purin-2-ylamine (2.7 g, 12.8 mmol), CuI (1.2 g, 13.4 mmol), I2 (3.3 g, 12.8 mmol), isoamyl nitrite (10.6 mL), and CH2I2 (5.3 g, 39.3 mmol) in THF (60 mL) were heated at reflux for 75 min. The mixture was cooled to rt, filtered through Celite, and adsorbed onto silica gel. Purification by chromatography (60% EtOAc/hexane) yielded an off-white solid (13.4 g, 54%): MS [M+H]+ 323; m.p.104° C.

Aufarbeitung

  1. temperatureat reflux for 75 min
  2. filtrationfiltered through Celite
  3. customPurification by chromatography (60% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7c58faed018d4b658eff37db9f430a0d
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115589B2

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