Sodium Hydroxide → HCID 46908750, compound

HRID 1159682Notes

Reaction equation

HRID 1159682 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]1[C:8]([CH2:9][C:10]([O:12]C)=[O:11])=[CH:7][N:6]=[C:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[O:23])=[CH:17][CH:16]=2)[N:4]=1.[OH-].[Na+]>O1CCCC1.CO>[CH3:33][N:2]([CH3:1])[C:3]1[C:8]([CH2:9][C:10]([OH:12])=[O:11])=[CH:7][N:6]=[C:5]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)=[O:23])=[CH:19][CH:20]=2)[N:4]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59514509HCID 59514509, compound

Product 1

HCID 46908750HCID 46908750, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl {4-(dimethylamino)-2-[4-({[(4-fluorobenzyl)oxy]carbonyl}amino)benzyl]-pyrimidin-5-yl}acetate (45 mg, 0.10 mmol) in tetrahydrofuran (0.5 mL) and methanol (0.5 mL) was added 1N NaOH aq. (0.2 mL). The reaction mixture was stirred for 20 hours at room temperature and concentrated under reduced pressure. The residue was neutralized with 1N hydrochloric acid and concentrated under reduced pressure. This residue was dissolved with chloroform/methanol (10:1) and the insoluble was removed by filtration. The filtrate was concentrated under reduced pressure to give {4-(dimethylamino)-2-[4-({[(4-fluoro-benzyl)oxy]carbonyl}amino)benzyl]pyrimidin-5-yl}acetic acid (35 mg, 80%) as a pale yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThis residue was dissolved with chloroform/methanol (10:1)
  4. customthe insoluble was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7b67b093782044f0b096a2ec16144e97
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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