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Ethanol → 6-(5-Carboxy-naphthalen-2-yloxy)-pyrimidine-4-carboxylic acid ethyl ester

HRID 1094516
Notes
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Reaction equation

HRID 1094516 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]3)[CH:3]=1.C[CH2:23][OH:24].CCN([CH2:30][CH3:31])CC.[C]=[O:33]>CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:30]([O:33][C:23]([C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[C:19]([OH:21])=[O:20])[CH:10]=2)[N:5]=[CH:6][N:7]=1)=[O:24])[CH3:31]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 248238946-(6-Chloropyrimidin-4-yloxy)-1-naphthoic acidHCID 178418416HCID 178418416, compound

Product 1

HCID 591759676-(5-Carboxy-naphthalen-2-yloxy)-pyrimidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418476
HCID 178418476, compound
Catalyst
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 10 g (33.3 mMol) 6-(6-chloro-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid (preparation see WO 2006/59234; Step 25.1), 150 ml EtOH, 9.03 ml (64:9 mMol) Et3N and 2.35 g (3.32 mMol) PdCl2(PPh3)2 is stirred under a atmosphere of 120 bar carbonmonoxide in an autoclave for 12 h at 115° C. The reaction mixture is diluted with 400 ml EtOAc, filtered through Hyflo and the residue washed with MeOH. The filtrate is concentrated and the residue suspended in 400 ml EtOAc and 200 ml water. Acidification to pH 4 with 4 N HCl and addition of MeOH produces a solution. The aq. layer is separated off and extracted with 3 portions of EtOAc. The organic phases are washed with water and brine, dried (Na2SO4), treated with char coal and concentrated. Trituration of the residue in EtOAc/ether and filtration gives the title compound: m.p.: 211-212° C.; MS: [M+1]+=339.

Workup

  1. filtrationfiltered through Hyflo
  2. washthe residue washed with MeOH
  3. concentrationThe filtrate is concentrated
  4. additionAcidification to pH 4 with 4 N HCl and addition of MeOH
  5. customproduces a solution
  6. customThe aq. layer is separated off
  7. extractionextracted with 3 portions of EtOAc
  8. washThe organic phases are washed with water and brine
  9. dry with materialdried (Na2SO4)
  10. additiontreated with char coal
  11. concentrationconcentrated
  12. filtrationTrituration of the residue in EtOAc/ether and filtration

Sources & evidence

ORD record
ord-6d870cb2a97b4b859419db8a671ae1d1
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08133886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes