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Citric Acid → (5-Amino-pyridin-3-yl)-(4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 82258
Notes
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Reaction equation

HRID 82258 reaction equation
C(=[N:14][C:15]1[CH:16]=[C:17]([C:21]([C:23]2[C:31]3[C:30]([Cl:32])=[N:29][CH:28]=[N:27][C:26]=3[N:25]([CH3:33])[CH:24]=2)=[O:22])[CH:18]=[N:19][CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.CCOCC>C1COCC1>[NH2:14][C:15]1[CH:16]=[C:17]([C:21]([C:23]2[C:31]3[C:30]([Cl:32])=[N:29][CH:28]=[N:27][C:26]=3[N:25]([CH3:33])[CH:24]=2)=[O:22])[CH:18]=[N:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 311Citric AcidHCID 3283Diethyl EtherHCID 86672119(4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanone

Product 1

HCID 86672120(5-Amino-pyridin-3-yl)-(4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of [5-(benzhydrylidene-amino)pyridin-3-yl]-(4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone (Preparation 229, 30 g, 0.066 mol) in THF (200 mL) was added aq. citric acid (200 mL), the mixture was stirred for 30 min at room temperature. Ether was added and the layers were separated. The aqueous layer was adjusted to pH7 by aqueous Na2CO3. Then the mixture was filtered. The filter cake was evaporated with toluene and the residue was washed with EtOAc (200 mL) to give the title compound as a brown solid in 95% yield, 18 g.

Workup

  1. customthe layers were separated
  2. filtrationThen the mixture was filtered
  3. customThe filter cake was evaporated with toluene
  4. washthe residue was washed with EtOAc (200 mL)

Sources & evidence

ORD record
ord-a1a9372cbdb047b5b5815df22e7e8239
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846698B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes