N-Iodosuccinimide → 4-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

HRID 1775170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1775170
[CH:1]1([C:6]2[C:7]3[CH:14]=[CH:13][NH:12][C:8]=3[N:9]=[CH:10][N:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:15]N1C(=O)CCC1=O>ClCCl>[CH:1]1([C:6]2[C:7]3[C:14]([I:15])=[CH:13][NH:12][C:8]=3[N:9]=[CH:10][N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 116369524-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 579632054-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidineAusbeute 371,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine (48, 0.099 g, 0.53 mmol) was dissolved in 3.4 mL of dichloromethane under an atmosphere of nitrogen and N-iodosuccinimide (0.131 g, 0.582 mmol) was added. The mixture was stirred overnight, then quenched with aqueous sodium thiosulfate. The aqueous layer was separated and washed with ethyl acetate. The organic layers were combined and washed with water, brine, dried over sodium sulfate and filtered. The filtrate was concentrated under vacuum to provide the desired compound (49, 0.616 g), used in the next step without further purification. MS (ESI) [M+H+]+=313.9.

Aufarbeitung

  1. customquenched with aqueous sodium thiosulfate
  2. customThe aqueous layer was separated
  3. washwashed with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3500742b585145759b34963dad71b717
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260437B2

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