Sodium Hydroxide → 2-(4-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acid

HRID 219656Notes

Reaction equation

HRID 219656 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][C:15]([F:18])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>CO>[F:18][C:15]1[CH:14]=[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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69279303Ethyl-2-(4-fluorophenyl)-4-methylpyrimidine-5-carboxylate

Product 1

HCID 300316142-(4-Fluorophenyl)-4-methylpyrimidine-5-carboxylic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl-2-(4-fluorophenyl)-4-methylpyrimidine-5-carboxylate (1.65 g, 6.35 mmol) in MeOH (75 mL) is treated with 2 N aqueous sodium hydroxide (10 mL) and heated to reflux for 30 min. MeOH is removed in vacuo and the residue is diluted with water (50 mL). The solution is adjusted to pH ˜2 with 2 M hydrochloric acid. The precipitated is collected by filtration, washed with water and vacuum dried to afford 2-(4-fluorophenyl)-4-methylpyrimidine-5-carboxylic acid (1.3 g, 88%) as a solid. MS: 233 (M+H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. customMeOH is removed in vacuo
  4. additionthe residue is diluted with water (50 mL)
  5. filtrationThe precipitated is collected by filtration
  6. washwashed with water and vacuum
  7. customdried

Sources & evidence

ORD record
ord-7b8000808ed0476f9b375b0775826a57
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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