Sodium Hydroxide → HCID 59514534, compound

HRID 1159680Notes

Reaction equation

HRID 1159680 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:32]=[CH:31][C:15]([CH2:16][C:17]2[N:22]=[C:21]([N:23]([CH3:25])[CH3:24])[C:20]([CH2:26][C:27]([O:29]C)=[O:28])=[CH:19][N:18]=2)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][C:17]2[N:22]=[C:21]([N:23]([CH3:24])[CH3:25])[C:20]([CH2:26][C:27]([OH:29])=[O:28])=[CH:19][N:18]=2)=[CH:31][CH:32]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59514555HCID 59514555, compound

Product 1

HCID 59514534HCID 59514534, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl [2-(4-{[(benzyloxy)carbonyl]amino}benzyl)-4-(dimethylamino)pyrimidin-5-yl]acetate (1.51 g, 3.48 mmol) in tetrahydrofuran (8 mL) and methanol (15 mL) was added 1N NaOH aq. (5 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 insolubles were removed by filtration. The filtrate was concentrated under reduced pressure. The residual solid was recrystallized with acetonitrile/ethanol (10:1) to give [2-(4-{[(benzyloxy)carbonyl]amino}benzyl)-4-(dimethylamino)pyrimidin-5-yl]acetic acid (1.14 g, 78%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThis residue was dissolved with chloroform/methanol (10:1)
  4. customthe insolubles were removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residual solid was recrystallized with acetonitrile/ethanol (10:1)

Sources & evidence

ORD record
ord-8747c60a8d9d40df9c6bdf80a6badd68
Source dataset
uspto-grants-2010_10
Patent number
US07812160B2

Reaction notes

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