Sodium Hydroxide → HCID 46908750, compound

HRID 2422169Notes

Reaction equation

HRID 2422169 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-fluorobenzyl)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-e0124c8e634d4a8c86c7e9bc09988b14
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

Loading…