Sodium Hydroxide → HCID 68965055, compound

HRID 226423Notes

Reaction equation

HRID 226423 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:19]=[C:18]([CH3:20])[C:17](/[CH:21]=[CH:22]/[C:23]([O:25]CC)=[O:24])=[CH:16][N:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][C:14]2[N:19]=[C:18]([CH3:20])[C:17](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:16][N:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86603726HCID 86603726, compound

Product 1

HCID 68965055HCID 68965055, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl (2E)-3-{2-[(1-benzyl-3-pyrrolidinyl)amino]-4-methyl-5-pyrimidinyl}acrylate (750 mg) and 1N NaOH solution (4.1 ml) in MeOH (10 ml) and THF (10 ml) was stirred at 80-85° C. for 2 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture was AcOEt and H2O. The aqueous solution was adjusted to PH 5.4 with 5% HCl solution and resultant solution was evaporated in vacuo and the residue was dissolved in a MeOH and THF. The solvent was evaporated in vacuo and dried to give (2E)-3-{2-[(1-benzyl-3-pyrrolidinyl)amino]-4-methyl-5-pyrimidinyl}acrylic acid (693 mg).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in a mixture
  3. customwas evaporated in vacuo
  4. dissolutionthe residue was dissolved in a MeOH and THF
  5. customThe solvent was evaporated in vacuo
  6. customdried

Sources & evidence

ORD record
ord-f7b34337d75a463385fc9c366568804b
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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