Methanol → 4-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acid

HRID 2381899Notes

Reaction equation

HRID 2381899 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:18])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[N:10][CH:11]=1)=[O:5])C.[Li+].[OH-].C1COCC1.CO>O>[CH3:18][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:8]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68555848HCID 68555848, compound

Product 1

HCID 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid ethyl ester (26.7 mmol) and LiOH (53.4 mmol) in a 1:1:1 solution of THF, MeOH and water (200 mL) is stir at rt overnight. The THF/MeOH is evaporated, and the aqueous solution is treated with 10% aqueous HCl to adjust the pH to between 1.5 and 2.5. The solid is filtered off, washed with water and dried in vacuo to yield 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5.50 g, 96%) as a solid. MS: 233 (M+H); 1H 1H NMR (300 MHz, CD3OD): δ=2.93(s, 3H), 7.59 (m, 1H), 8.05 (t, 1H), 8.62 (d, 1H), 8.76 (d, 1H), 9.28 (s, 1H).

Workup

  1. customThe THF/MeOH is evaporated
  2. additionthe aqueous solution is treated with 10% aqueous HCl
  3. filtrationThe solid is filtered off
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ef900d06a23148428fd9ca09904bb259
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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