Lithium Hydroxide → HCID 66901646, compound

HRID 1692386Notes

Reaction equation

HRID 1692386 reaction equation
C[O:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[CH:7][C:6]=1[C:22]1[CH:23]=[N:24][CH:25]=[N:26][CH:27]=1)=[O:4].[OH-].[Li+].Cl.O>C1COCC1.CO>[CH3:11][C:10]1[C:5]([C:3]([OH:4])=[O:2])=[C:6]([C:22]2[CH:23]=[N:24][CH:25]=[N:26][CH:27]=2)[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21885828Hydrate;hydrochlorideHCID 66901551HCID 66901551, compound

Product 1

HCID 66901646HCID 66901646, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.43 g (1.20 mmol) of 5-methyl-3-pyrimidin-5-yl-3′-trifluoromethyl-biphenyl-4-carboxylic acid methyl ester in 12 ml of THF/MeOH (1:1) was added 2.89 ml (2.90 mmol) of lithium hydroxide solution (1 molar in water) drop by drop and the reaction mixture was then heated up to 50° C. After 40 hours, the reaction mixture was poured into crashed ice and acidified with HCl/H2O (1N) to pH 3.0 and then extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 3:2) to give 0.410 g (99%) of the title compound as colorless solid. MS: 357.0 (M−H−).

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 3:2)

Sources & evidence

ORD record
ord-da3a60baf233482aa3fc804731dd40aa
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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