(5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanol → (5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone

HRID 82237Notes

Reaction equation

HRID 82237 reaction equation
[C:1]1([C:7](=[N:14][C:15]2[CH:16]=[C:17]([CH:21]([C:23]3[C:31]4[CH:30]=[N:29][CH:28]=[N:27][C:26]=4[NH:25][CH:24]=3)[OH:22])[CH:18]=[N:19][CH:20]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC#N.O=[Mn]=O>[C:1]1([C:7](=[N:14][C:15]2[CH:16]=[C:17]([C:21]([C:23]3[C:31]4[CH:30]=[N:29][CH:28]=[N:27][C:26]=4[NH:25][CH:24]=3)=[O:22])[CH:18]=[N:19][CH:20]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 86672110(5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanol

Product 1

HCID 86672111(5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanoneYield 61%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of (5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanol (Preparation 194, 1820 mg, 4.5 mmol) in MeCN (45 mL) was added MnO2 (1960 mg, 22.5 mmol) portionwise and the resulting mixture stirred at 50° C. overnight. Another portion of MnO2 (1960 mg, 22.5 mmol) was added to the reaction and the mixture heated to reflux for 5 hr. After cooling to room temperature, the reaction mixture was filtered through a pad of arbocel, the filter cake rinsed with DCM (100 mL) and the resulting filtrate concentrated in vacuo. The resulting material was purified by column chromatography on silica gel (gradient of EtOAc:MeOH 100:0 to 90:10) to give the desired compound as a solid in 61% yield, 1120 mg.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 5 hr
  3. temperatureAfter cooling to room temperature
  4. filtrationthe reaction mixture was filtered through a pad of arbocel
  5. washthe filter cake rinsed with DCM (100 mL)
  6. concentrationthe resulting filtrate concentrated in vacuo
  7. customThe resulting material was purified by column chromatography on silica gel (gradient of EtOAc:MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-8b027b21c73e49ac9c363c086eb8f10c
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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