Methanol → 2-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid

HRID 219660Notes

Reaction equation

HRID 219660 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:19])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+].C1COCC1.CO>O>[F:18][C:14]1[CH:13]=[C:12]([C:9]2[N:8]=[C:7]([CH3:19])[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 685575422-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 617025872-(3-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid ethyl ester (6.7 g, 27.2 mmol) and NaOH (2.1 g, 54.4 mmol) in a 1:1:1 solution of THF, MeOH and water (300 mL) is heated at reflux for 45 min. The THF/MeOH is evaporated, and the aqueous solution is treated with 3 N HCl to adjust the pH to between 2 and 3. The solid is filtered off, washed with water and dried in vacuo to yield 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5.4 g, 91%) as a solid. MS: 233 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.85 (s, 3H), 7.24 (m, 1H), 7.50 (m, 1H), 8.17 (m, 1H), 8.32 (m, 1H), 9.20 (s, 1H).

Workup

  1. temperatureat reflux for 45 min
  2. customThe THF/MeOH is evaporated
  3. additionthe aqueous solution is treated with 3 N HCl
  4. filtrationThe solid is filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4fc9626349df49ada3f8433d50afca4a
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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