Hydrochloric Acid → 6-(2-Fluoropyrimidin-4-yloxy)-1-naphthoic acid

HRID 1925288Notes

Reaction equation

HRID 1925288 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]2.C([O-])([O-])=O.[Cs+].[Cs+].[F:21][C:22]1[N:27]=[C:26](F)[CH:25]=[CH:24][N:23]=1.Cl>CS(C)=O.O>[F:21][C:22]1[N:27]=[C:26]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:8]([C:12]([OH:14])=[O:13])=[CH:7][CH:6]=[CH:5]3)[CH:25]=[CH:24][N:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 1377162,4-DifluoropyrimidineHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 675205426-(2-Fluoropyrimidin-4-yloxy)-1-naphthoic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 6-hydroxy-1-napthoic acid (3.23 g, 17.2 mmol) in DMSO (8 mL), Cs2CO3 (16.8 g, 57.6 mmol) was added and stirred at RT 10 min. 2,4-Difluoropyrimidine (2 g, 17.2 mmol) was added and the reaction was stirred at RT for 12 h. The mixture was diluted with water and made pH 7 using 1 N HCl, at which point it is a foamy emulsion. The mixture sat without stirring 2 days and the resulting solid was filtered and rinsed with water and Et2O to yield the title compound as a pink solid.

Workup

  1. stirringthe reaction was stirred at RT for 12 h
  2. stirringwithout stirring 2 days
  3. filtrationthe resulting solid was filtered
  4. washrinsed with water and Et2O

Sources & evidence

ORD record
ord-c6ebd87ecfd647c4aff53885506094a2
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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