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Sodium Hydroxide → 3-{[5-(4-Fluorophenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid

HRID 2189087
Notes
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Reaction equation

HRID 2189087 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=4)=[C:20]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1.[OH-].[Na+]>C1COCC1>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:14]3[C:13]([NH:12][C:8]4[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=4)[O:5][CH2:4][C:3]([OH:35])=[O:2])=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:27][CH:26]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 582801063-{[5-(4-Fluorophenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

Product 1

HCID 582802343-{[5-(4-Fluorophenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 21.1 mg (0.045 mmol) of 3-{[5-(4-fluorophenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester in 1 ml of THF, add 0.135 ml of 1N sodium hydroxide solution at RT and stir at 50° C. for 1 h. Cool to RT and remove the THF under reduced pressure. Add water to the residue, and then, with ice cooling, 1N hydrochloric acid. Filter off the precipitated solid, wash repeatedly with water and dry at 40° C. under reduced pressure. 11.5 mg (56.2% of theory) of the target compound are obtained as a white solid.

Workup

  1. temperatureCool to RT
  2. customremove the THF under reduced pressure
  3. filtrationFilter off the precipitated solid
  4. washwash repeatedly with water
  5. customdry at 40° C. under reduced pressure
  6. custom11.5 mg (56.2% of theory) of the target compound are obtained as a white solid

Sources & evidence

ORD record
ord-d16e70e8c9a545198337d9cd564b5b59
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324222B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes