Lithium Hydroxide → 2-(Pyridin-4-yl)pyrimidine-5-carboxylic acid

HRID 219639

Reaction equation

HRID 219639 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[N:9][CH:10]=1)=[O:4].[Li+].[OH-]>CO>[N:14]1[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][CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69122655Methyl 2-(pyridin-4-yl)pyrimidine-5-carboxylate

Product 1

HCID 227102132-(Pyridin-4-yl)pyrimidine-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-pyridin-4-yl-pyrimidine-5-carboxylic acid methyl ester (1.11 g, 5.18 mmol), and aqueous LiOH (1 M, 5.18 mL) in MeOH (7.25 mL) is stirred at room temperature overnight. MeOH is removed in vacuo, and the aqueous solution is treated with 3 N HCl to adjust the pH to between 2 and 3. The solid is filtered off and washed with water and dried in vacuum to yield 2-pyridin-4-yl-pyrimidine-5-carboxylic acid (1 g, 96%) as a solid. MS: 202 (M+H).

Workup

  1. customMeOH 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-491d2d1456254b5c9f5411093db16779
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Linked notes

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