Sodium Hydroxide → HCID 21075028, compound

HRID 1171468Notes

Reaction equation

HRID 1171468 reaction equation
Br[C:2]1[C:3]([C:12]([OH:14])=[O:13])=[N:4][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[N:6][CH:7]=1.[OH-].[Na+]>CO.[Pd]>[C:8]([C:5]1[N:4]=[C:3]([C:12]([OH:14])=[O:13])[CH:2]=[CH:7][N:6]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 122589145-Bromo-2-(tert-butyl)pyrimidine-4-carboxylic acid

Product 1

HCID 21075028HCID 21075028, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-bromo-2-tert-butyl-pyrimidine-4-carboxylic acid (1.65 g, 6.37 mmol) and aqueous sodium hydroxide (1.0 N, 19.1 mL, 19.1 mmol) in methanol (100 ml) was treated with a catalytic amount of 10% palladium on carbon. The mixture was degassed under vacuum/nitrogen, then hydrogenated at 50 psi for 2 hours. The catalyst was removed by filtration, the methanol was removed under vacuum, and the aqueous was acidified by the addition of 1.0 N aqueous hydrochloric acid (40 mL). The resulting suspension was extracted with ethyl acetate (4×50 mL), the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated in-vacuo to yield 1.06 g of 2-tert-butylpyrimidine-4-carboxylic acid as a white powder. MS (ES+)=181 (M+H+).

Workup

  1. customThe mixture was degassed under vacuum/nitrogen
  2. customThe catalyst was removed by filtration
  3. customthe methanol was removed under vacuum
  4. additionthe aqueous was acidified by the addition of 1.0 N aqueous hydrochloric acid (40 mL)
  5. extractionThe resulting suspension was extracted with ethyl acetate (4×50 mL)
  6. washthe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-24636675f20949539a0f26cb43e6cdc2
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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