Water → 2-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

HRID 82234

Reaktionsgleichung

Reaktionsgleichung von HRID 82234
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32]([NH:34][C:35]2[CH:36]=[N:37][CH:38]=[C:39]([C:41]([C:43]3[C:51]4[CH:50]=[N:49][CH:48]=[N:47][C:46]=4[N:45]([CH:52]([CH3:54])[CH3:53])[CH:44]=3)=[O:42])[CH:40]=2)=[O:33])[CH:28]=[CH:29][CH:30]=1.O>ClCCl>[CH:24]([C:25]1[CH:26]=[C:27]([CH2:31][C:32]([NH:34][C:35]2[CH:36]=[N:37][CH:38]=[C:39]([C:41]([C:43]3[C:51]4[CH:50]=[N:49][CH:48]=[N:47][C:46]=4[N:45]([CH:52]([CH3:54])[CH3:53])[CH:44]=3)=[O:42])[CH:40]=2)=[O:33])[CH:28]=[CH:29][CH:30]=1)=[O:23]

Komponenten

5

Edukt 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 708177872-[3-(hydroxymethyl)phenyl]-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide

Produkt 1

HCID 866720722-(3-formylphenyl)-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Dess Martin Periodinane (392 mg, 0.93 mmol) was added to a solution of (2-[3-(hydroxymethyl)phenyl]-N-{5-[(7-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)carbonyl]pyridin-3-yl}acetamide (Preparation 193, 265 mg, 0.62 mmol) in dichloromethane (15 mL) and the mixture was stirred at room temperature for 18 hours. Water (10 mL) was added and the aqueous layer extracted with a 95:5 mixture of dichloromethane/methanol (3×10 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography using silica gel (gradient of dichloromethane to dichloromethane/methanol (10:1 to 9:1) to afford the title compound as a brown solid in 80% yield, 211 mg.

Aufarbeitung

  1. extractionthe aqueous layer extracted with a 95:5 mixture of dichloromethane/methanol (3×10 mL)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c9f39f745fd14be8be18f5ce3ebd860b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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