Triethylamine → Methyl 2-(pyrimidin-4-yl)benzoate

HRID 60583Notes

Reaction equation

HRID 60583 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.C(N(CC)CC)C>CO.[C].[Pd]>[N:7]1[CH:2]=[CH:3][C:4]([C:8]2[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12][CH3:13])=[O:11])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 24902049Methyl 2-(6-chloropyrimidin-4-yl)benzoate

Product 1

HCID 86680852Methyl 2-(pyrimidin-4-yl)benzoateYield 94.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 2-(6-chloropyrimidin-4-yl)benzoate (0.60 g), triethylamine (1.7 mL) and 10% palladium carbon (containing water (50%), 0.26 g) in methanol (20 mL) was stirred at room temperature for 1 hr under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate, and the mixture was washed with saturated brine. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (0.49 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate
  4. washthe mixture was washed with saturated brine
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-31a3f91cb91248cda44e48aec57eba75
Source dataset
uspto-grants-2016_09
Patent number
US09440990B2

Reaction notes

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