Sodium Hydroxide → 4-(2-Fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid

HRID 1036622Notes

Reaction equation

HRID 1036622 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])=[N:8][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:10][C:11]=1[CH3:12])=[O:5])C.[OH-].[Na+]>C(O)C.O>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:11]([CH3:12])[N:10]=[C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 594212924-(2-Fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 594211804-(2-Fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acidYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(2-fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid ethyl ester (0.6 g, 10.96 mmol), and solid NaOH (2 g, 50 mmol) in ethanol (5 mL) and water (1 mL) was refluxed for 1 h, then cooled to room temperature. The solvent was removed under reduced pressure, and the residue was acidified with a 6N HCl solution. Then, the product was extracted with EtOAC (3×25 mL) and the organic extracts were dried and concentrated to give 4-(2-fluorophenyl)-6-methyl-2-morpholin-4-yl-pyrimidine-5-carboxylic acid (0.43 g, 78%) as white solid. Mass Spec. LCMS 318 (M+1).

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe solvent was removed under reduced pressure
  3. extractionThen, the product was extracted with EtOAC (3×25 mL)
  4. customthe organic extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b96f766c649d42329e8bfbcf3c4e1a0b
Source dataset
uspto-grants-2013_10
Patent number
US08546414B2

Reaction notes

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