Lithium hydroxide, monohydrate → 6-((Tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid

HRID 1868462Notes

Reaction equation

HRID 1868462 reaction equation
[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:31])=[N:11][C:12]2[N:13]([CH:23]=[C:24]([C:26]([O:28]CC)=[O:27])[N:25]=2)[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:31])=[N:11][C:12]2[N:13]([CH:23]=[C:24]([C:26]([OH:28])=[O:27])[N:25]=2)[C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67021509Ethyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 670215506-((Tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acidYield 101.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylate (100 mg, 021 mmol) in THF (2 mL) and H2O (0.5 mL) at room temperature was added LiOH.H2O (18 mg, 0.42 mmol). After 16 h, the reaction was concentrated under reduced pressure and diluted with EtOAc. The organic layer was washed with 1N HCl and brine prior to drying over anhydrous MgSO4. Filtration, concentration under reduced pressure gave 6-((tert-butoxycarbonyl)methyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxylic acid (95 mg, 100%) as a light yellow solid.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with 1N HCl and brine
  4. dry with materialto drying over anhydrous MgSO4
  5. filtrationFiltration, concentration under reduced pressure

Sources & evidence

ORD record
ord-50b54d2ccb314059be3e97a8a6891d3e
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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