Diiodomethane → 6-chloro-8-(3-fluorophenyl)-2-iodo-9-methyl-9H-purine

HRID 1369381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1369381
[Cl:1][C:2]1[N:10]=[C:9](N)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[N:6]2[CH3:12].[I:20]CI.N(OCCC(C)C)=O>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]([I:20])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[N:6]2[CH3:12]

Komponenten

6

Edukt 3

HCID 6346DiiodomethaneHCID 8053Isoamyl NitriteHCID 10492805HCID 10492805, Verbindung

Produkt 1

HCID 99522656-chloro-8-(3-fluorophenyl)-2-iodo-9-methyl-9H-purineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Chloro-8-(3-fluorophenyl)-9-methyl-9H-2-purinyl-amine (960 g) was dissolved in 9.6 liters of tetrahydrofuran and then 774.3 g of cuprous iodide and 1.49 liters of diiodomethane were added thereto. Isoamyl nitrite (1.49 liters) was added dropwise during 1 hour into the mixture with heating under reflux. The reaction solution was heated under reflux for 15 minutes, cooled, diluted with 4 liters of ethyl acetate and then filtered through Celite followed by washing with ethyl acetate three times (3×2 liters). The filtrate and the washings were combined and washed with 8 liters of water and 8 liters of brine. The organic layer was dried over 2 kg of anhydrous sodium sulfate and concentrated to about 3 liters. The concentrated solution was diluted with 10 liters of hexane and the resulting crystals were filtered and washed with 1 liter of hexane. The crystals were then dried at 50° C. for 4 hours to give 1076 g of 6-chloro-8-(3-fluorophenyl)-2-iodo-9-methyl-9H-purine. The yield was 75%.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureThe reaction solution was heated
  4. temperatureunder reflux for 15 minutes
  5. temperaturecooled
  6. filtrationfiltered through Celite
  7. washby washing with ethyl acetate three times (3×2 liters)
  8. washwashed with 8 liters of water and 8 liters of brine
  9. dry with materialThe organic layer was dried over 2 kg of anhydrous sodium sulfate
  10. concentrationconcentrated to about 3 liters
  11. additionThe concentrated solution was diluted with 10 liters of hexane
  12. filtrationthe resulting crystals were filtered
  13. washwashed with 1 liter of hexane
  14. customThe crystals were then dried at 50° C. for 4 hours

Quellen und Nachweise

ORD-Eintrag
ord-8fef669b7dc2463e96e76a0d206f45e6
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06579868B1

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