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

HRID 82236

Reaction equation

HRID 82236 reaction equation
[N:1]1[C:6]2[NH:7][CH:8]=[CH:9][C:5]=2[CH:4]=[N:3][CH:2]=1.[C:10]1([C:16](=[N:23][C:24]2[CH:25]=[N:26][CH:27]=[C:28]([CH:31]=2)[CH:29]=[O:30])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].[Cl-].[NH4+]>CO>[C:10]1([C:16](=[N:23][C:24]2[CH:31]=[C:28]([CH:29]([C:9]3[C:5]4[CH:4]=[N:3][CH:2]=[N:1][C:6]=4[NH:7][CH:8]=3)[OH:30])[CH:27]=[N:26][CH:25]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 2615917H-Pyrrolo(2,3-d)pyrimidineHCID 866721015-((Diphenylmethylene)amino)nicotinaldehyde

Product 1

HCID 86672110(5-((Diphenylmethylene)amino)pyridin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanolYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7H-pyrrolo[2,3-d]pyrimidine (Preparation 202, 953 mg, 8.0 mmol), 5-[(diphenylmethylene)amino]nicotinaldehyde (Preparation 106, 3340 mg, 11.7 mmol) and KOH (1350 mg, 24 mmol) in MeOH (16 mL) was stirred for 16 hours at room temperature. The reaction was neutralized with saturated aqueous ammonium chloride solution and the mixture was extracted with EtOAc (3×200 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to obtain a crude residue. The crude material was purified by column chromatography on silica gel (EtOAc:MeOH=100:0 to 80:20,) to give the desired compound as a solid in 62% yield, 2003 mg.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×200 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a crude residue
  5. customThe crude material was purified by column chromatography on silica gel (EtOAc:MeOH=100:0 to 80:20,)

Sources & evidence

ORD record
ord-c70979a564954ea4a279e7475fa73bef
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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