Lithium hydroxide, monohydrate → HCID 67021393, compound

HRID 1868454Notes

Reaction equation

HRID 1868454 reaction equation
[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:29])=[N:11][C:12]2[N:13]([N:23]=[C:24]([C:26]([O-: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].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([CH2:8][C:9]1[C:10]([CH3:29])=[N:11][C:12]2[N:13]([N: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 86761032HCID 86761032, compound

Product 1

HCID 67021393HCID 67021393, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 6-((tert-butoxycarbonyl)methyl)-7-(2,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylate (13 mg, 0.03 mmol) in THF (1 mL) was added LiOH-H2O (9 mg, 0.21 mmol) in H2O (0.1 mL). After heating to 40° C. for 1 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 afforded 6-((tert-butoxycarbonyl)methyl)-7-(2,4-dichlorophenyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carboxylic acid (13 mg, 100%) as a white 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-c21300aac43740cb828477dee99758c2
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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