Hydrochloric Acid → 4-(4-Chloro-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclohexanone

HRID 51536Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51536
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:12]3[CH2:21][CH2:20][C:15]4(OCC[O:16]4)[CH2:14][CH2:13]3)[C:4]=2[N:5]=[CH:6][N:7]=1.Cl>O1CCCC1.CC(C)=O>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH:12]3[CH2:13][CH2:14][C:15](=[O:16])[CH2:20][CH2:21]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 227363864-chloro-5-iodo-7-(1,4-dioxaspiro[4.5]decan-8-yl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 227364134-(4-Chloro-5-iodo-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclohexanoneAusbeute 68,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-7-(1,4-dioxaspiro[4.5]dec-8-yl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (20 g, 47.7 mmol) and 6 N HCl(aq) (60 mL, 360 mmol) in tetrahydrofuran (120 mL) and acetone (600 mL) was stirred at ambient temperature under an atmosphere of nitrogen for 17 hours. The solvent was removed under reduced pressure and 6NHCl(aq) (20 mL), tetrahydrofuran (60 mL), and acetone (300 mL) were added to the mixture. The mixture was stirred at ambient temperature under an atmosphere of nitrogen for 4.5 hour. The solvent was removed under reduced pressure and the yellow colored residue was washed with water to yield 4-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-cyclohexanone (12.3 g, 32.7 mmol). RP-HPLC (Hypersil C18, 5 μm, 250×4.6 mm; 25%-100% over 15 min with 0.05 M ammonium acetate, 1 mL/min) Rt 10.20 min.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure and 6NHCl(aq) (20 mL), tetrahydrofuran (60 mL), and acetone (300 mL)
  2. additionwere added to the mixture
  3. stirringThe mixture was stirred at ambient temperature under an atmosphere of nitrogen for 4.5 hour
  4. customThe solvent was removed under reduced pressure
  5. washthe yellow colored residue was washed with water

Quellen und Nachweise

ORD-Eintrag
ord-acb9463d9ed64939a990942db18f38d8
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713474B2

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