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

HRID 1361628Notes

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

Participants

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

temperatureThe reaction mixture was cooled to RT
customThe product was precipitated from the solution
washThe mixture was then washed with 20 mL of water twice
filtrationThe solid was collected by filtration
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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