Sodium Hydroxide → 5-(Pyrimidin-2-yl)pyridine-3-carboxylic acid

HRID 454526Notes

Reaction equation

HRID 454526 reaction equation
[OH-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[C:9]1[CH:10]=[C:11]([C:15]([O:17]C)=[O:16])[CH:12]=[N:13][CH:14]=1>O1CCOCC1.CO>[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[C:9]1[CH:10]=[C:11]([C:15]([OH:17])=[O:16])[CH:12]=[N:13][CH:14]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66989995Methyl 5-(pyrimidin-2-yl)pyridine-3-carboxylate

Product 1

HCID 669912565-(Pyrimidin-2-yl)pyridine-3-carboxylic acidYield 25%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (0.21 mL) was added to a solution mixture of the obtained methyl 5-(pyrimidin-2-yl)pyridine-3-carboxylate (30 mg) in dioxane (0.3 mL) and methanol (0.3 mL) at room temperature, followed by stirring at the same temperature for 1 hour and 30 minutes. The solvent was evaporated under reduced pressure, and water and toluene were added to the residue. The aqueous layer was separated and adjusted to a pH of 3.8 with 1 mol/L hydrochloric acid. The solid substance was collected by filtration to obtain 7.0 mg of 5-(pyrimidin-2-yl)pyridine-3-carboxylic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and water and toluene
  2. additionwere added to the residue
  3. customThe aqueous layer was separated
  4. filtrationThe solid substance was collected by filtration

Sources & evidence

ORD record
ord-73f62f057064405a985188929029d79c
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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