Methanol → 3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid sodium salt

HRID 2189093Notes

Reaction equation

HRID 2189093 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=4)[O:22][CH2:23][C:24]([OH:26])=[O:25])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:5][CH:4]=1.CO.O.[OH-].[Na+:40]>C1COCC1>[Na+:40].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:16]([NH:18][C:19]4[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=4)[O:22][CH2:23][C:24]([O-:26])=[O:25])=[N:15][CH:14]=[N:13][C:12]=3[O:11][C:10]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 582800653-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid

Product 1

HCID 671600413-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid sodium salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Suspend 2.52 g (5.39 mmol) of 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid in a mixture of 10 ml of THF, 10 ml of methanol and 1 ml of water at RT, add 5.39 ml of 1N sodium hydroxide solution dropwise and stir the resulting solution at RT for 10 min, before filtering off with suction through a fine frit (removal of suspended particles). Concentrate the solution under reduced pressure and treat the residue with ethanol. Filter off the insoluble solid with suction, wash with a little ethanol and dry under reduced pressure, then under high vacuum. Concentrate the filtrate, stir the residue again with a little ethanol and thus obtain a second product batch after filtering off with suction. After combining the two fractions, a total of 2.32 g (87.9% of theory) of the target compound are obtained as a colourless solid.

Workup

  1. filtrationbefore filtering off with suction through a fine frit (removal of suspended particles)
  2. concentrationConcentrate the solution under reduced pressure
  3. additiontreat the residue with ethanol
  4. filtrationFilter off the insoluble solid with suction
  5. washwash with a little ethanol
  6. customdry under reduced pressure
  7. concentrationConcentrate the filtrate
  8. stirringstir the residue again with a little ethanol
  9. customthus obtain a second product batch
  10. filtrationafter filtering off with suction
  11. customa total of 2.32 g (87.9% of theory) of the target compound are obtained as a colourless solid

Sources & evidence

ORD record
ord-39ab62b7e3d74f9ba6ac2cfbac6f0819
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

Loading…