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4-Hydroxybenzoic Acid → 4-(3-(Pyrimidin-4-yl)pyridin-2-yloxy)benzoic acid

HRID 1361628
Notes
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Reaction equation

HRID 1361628 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.CCOC(C)=O>[N:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]([O:14][C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)=[N:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 10796Cesium carbonateHCID 161089744-(2-Chloropyridin-3-yl)pyrimidine

Product 1

HCID 583968474-(3-(Pyrimidin-4-yl)pyridin-2-yloxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-(2-chloro-pyridin-3-yl)-pyrimidine, 4-hydroxy-benzoic acid and Cs2CO3 in DMSO was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 200° C. for 10 minutes. The reaction mixture was cooled to RT and diluted with 60 mL of EtOAc. The product was precipitated from the solution. The mixture was then washed with 20 mL of water twice. The solid was collected by filtration and dried in an oven at 50° C. to afford off white solid as desired product. MS m/z=294 [M+1]+. Calc'd for C16H11N3O3: 293.28.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customThe product was precipitated from the solution
  3. washThe mixture was then washed with 20 mL of water twice
  4. filtrationThe solid was collected by filtration
  5. customdried in an oven at 50° C.

Sources & evidence

ORD record
ord-c4af0462e1d44b2f9a7fbb1961e70bff
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07880000B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes