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

HRID 499238Notes

Reaction equation

HRID 499238 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])=[N:8][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>CO>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[N:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 594211844-(2-Fluoro-phenyl)-2-morpholin-4-yl-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 217124094-(2-Fluorophenyl)-2-morpholinopyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(2-Fluoro-phenyl)-2-morpholin-4-yl-pyrimidine-5-carboxylic acid ethyl ester was dissolved in a mixture of methanol (150 mL) and a 33% aqueous NaOH solution (150 mL). The mixture was heated at reflux for 3 hours, and allowed to cool to room temperature overnight. The solution was concentrated to ca. half the volume under reduced pressure. The resulting suspension was adjusted to pH 7 with a 1-5N aqueous HCl solution. The formed precipitate was filtered off, washed with water (3×), and air-dried at 45° C. overnight to give 4-(2-fluoro-phenyl)-2-morpholin-4-yl-pyrimidine-5-carboxylic acid as a tan solid (9.051 g, 29.8 mmol, 74% over 3 steps).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe solution was concentrated to ca. half the volume under reduced pressure
  4. filtrationThe formed precipitate was filtered off
  5. washwashed with water (3×)
  6. customair-dried at 45° C. overnight

Sources & evidence

ORD record
ord-9ddd375cd5c3453aa2b897756ab51a9c
Source dataset
uspto-grants-2010_08
Patent number
US07767680B2

Reaction notes

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