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

HRID 2189106Notes

Reaction equation

HRID 2189106 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[C:13]3[C:20]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=4)=[C:19]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[O:18][C:14]=3[N:15]=[CH:16][N:17]=2)[CH:6]=1.[OH-].[Na+]>C1COCC1>[CH3:28][O:27][C:24]1[CH:23]=[CH:22][C:21]([C:20]2[C:13]3[C:12]([NH:11][C:7]4[CH:6]=[C:5]([CH2:4][C:3]([OH:35])=[O:2])[CH:10]=[CH:9][CH:8]=4)=[N:17][CH:16]=[N:15][C:14]=3[O:18][C:19]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 250953893-{[5-(4-Methoxy-phenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenylacetic acid methyl ester

Product 1

HCID 250956423-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenylacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 50 mg (0.107 mmol) of 3-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenylacetic acid methyl ester in 2 ml of THF, add 0.322 ml of 1N sodium hydroxide solution at RT and stir at 50° C. for 4 h. Cool to RT and remove the THF under reduced pressure. Add water to the residue, and then 1N hydrochloric acid. Filter off the precipitated solid, wash with water and dry at 50° C. under reduced pressure. 41.7 mg (86% 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 with water
  5. customdry at 50° C. under reduced pressure
  6. custom41.7 mg (86% of theory) of the target compound are obtained as a white solid

Sources & evidence

ORD record
ord-090d652094cb4647b554ab5566319c83
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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