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

HRID 219642Notes

Reaction equation

HRID 219642 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 room temperature overnight. The MeOH is removed in vacuo, and the aqueous solution is treated with 3 N 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 HCl
  3. filtrationThe solid is filtered off
  4. washwashed with water
  5. customdried in vacuum

Sources & evidence

ORD record
ord-f25a8ea004ff4b26ae05e9319ef459cf
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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