Lithium Hydroxide → 2-(Pyridin-3-YL)pyrimidine-5-carboxylic acid

HRID 2381892Notes

Reaction equation

HRID 2381892 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:9][CH:10]=1)=[O:4].[Li+].[OH-]>CO>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:8]2[N:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 685565272-Pyridin-3-yl-pyrimidine-5-carboxylic acid methyl ester

Product 1

HCID 249036372-(Pyridin-3-YL)pyrimidine-5-carboxylic acidYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-pyridin-3-yl-pyrimidine-5-carboxylic acid methyl ester (0.73 g, 3.32 mmol) and 1M aqueous LiOH (3.32 mL) in MeOH (5 mL) is stirred at rt overnight. The MeOH is removed in vacuo, and the aqueous solution is treated with 3 N aqueous HCl to adjust the pH ˜2-3. The solid is filtered off and washed with water and dried in vacuum to yield 2-pyridin-3-yl-pyrimidine-5-carboxylic acid (0.2 g, 30%) as a solid. MS: 202 (M+H).

Workup

  1. customThe MeOH is removed in vacuo
  2. additionthe aqueous solution is treated with 3 N aqueous HCl
  3. filtrationThe solid is filtered off
  4. washwashed with water
  5. customdried in vacuum

Sources & evidence

ORD record
ord-1849d807d57549dc84caee64faeec841
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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