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

HRID 82234

Reaction equation

HRID 82234 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c9f39f745fd14be8be18f5ce3ebd860b
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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