Sodium Hydroxide → HCID 25095646, compound

HRID 2189110Notes

Reaction equation

HRID 2189110 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[C:15]2[C:22]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[C:21]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:20][C:16]=2[N:17]=[CH:18][N:19]=1.[OH-].[Na+]>C1COCC1>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]2[C:15]3[C:14]([NH:13][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=4[CH2:6][CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[N:19][CH:18]=[N:17][C:16]=3[O:20][C:21]=2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25095645HCID 25095645, compound

Product 1

HCID 25095646HCID 25095646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 28.9 mg (0.059 mmol) of 4-(2-{[5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)butanoic acid methyl ester in 1 ml of THF, add 0.176 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 1N hydrochloric acid. Filter off the precipitated solid, wash repeatedly with water and dry at 40° C. under reduced pressure overnight. 16.9 mg (60.2% 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 overnight
  6. custom16.9 mg (60.2% of theory) of the target compound are obtained as a white solid

Sources & evidence

ORD record
ord-b4c8f50f39dd4e13823a75d1bd55a9c2
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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