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

HRID 2189084Notes

Reaction equation

HRID 2189084 reaction equation
C[O:2][C:3](=[O:34])[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][CH:25]=[CH:24][CH:23]=4)=[C:20]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1.[OH-].[Na+]>C1COCC1>[C:22]1([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:34])=[O:2])=[N:18][CH:17]=[N:16][C:15]=3[O:19][C:20]=2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 582802413-[(5,6-Diphenylfuro[2,3-d]pyrimidin-4-yl)amino]phenoxyacetic acid methyl ester

Product 1

HCID 582801903-[(5,6-Diphenylfuro[2,3-d]pyrimidin-4-yl)amino]phenoxyacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 50 mg (0.111 mmol) of 3-[(5,6-diphenylfuro[2,3-d]pyrimidin-4-yl)amino]phenoxyacetic acid methyl ester in 2 ml of THF, add 0.33 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 under reduced pressure. 39.4 mg (81.3% 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 under reduced pressure
  6. custom39.4 mg (81.3% of theory) of the target compound are obtained as a white solid

Sources & evidence

ORD record
ord-35dcfe3dd4e546489a9bdbaa5236f22c
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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