Potassium Hydroxide → HCID 53404083, compound

HRID 1865300Notes

Reaction equation

HRID 1865300 reaction equation
[OH-].[K+].C[O:4][C:5]([C:7]1[C:8]([CH3:18])=[N:9][C:10]([C:14]([F:17])([F:16])[F:15])=[N:11][C:12]=1[CH3:13])=[O:6]>CCO.O>[CH3:13][C:12]1[C:7]([C:5]([OH:6])=[O:4])=[C:8]([CH3:18])[N:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[N:11]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 68576045HCID 68576045, compound

Product 1

HCID 53404083HCID 53404083, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

step B—A solution of KOH (1.74 g, 31.01 mmol) and water (10 mL) was added at RT to a solution of 4,6-dimethyl-2-trifluoromethyl-pyrimidine-5-carboxylic acid methyl ester (2.42 g, 10.33 mmol) in EtOH (20 mL). The resulting mixture was stirred at 40° C. overnight then cooled to RT and evaporated. The residue was partitioned between EtOAc and water. The aqueous layer was evaporated and the residue was taken up in H2O (1 mL). Concentrated HCl was added dropwise until crystals started to form. The mixture was diluted with H2O (5 mL) and stored in a refrigerator overnight. The crystals were filtered, rinsed with ice-cold water then ice-cold Et2O, and dried to afford 1.5 g (66%) of 4,6-dimethyl-2-trifluoromethyl-pyrimidine-5-carboxylic acid.

Workup

  1. temperaturethen cooled to RT
  2. customevaporated
  3. customThe residue was partitioned between EtOAc and water
  4. customThe aqueous layer was evaporated
  5. additionConcentrated HCl was added dropwise until crystals
  6. customto form
  7. customstored in a refrigerator overnight
  8. filtrationThe crystals were filtered
  9. washrinsed with ice-cold water
  10. customice-cold Et2O, and dried

Sources & evidence

ORD record
ord-721bacf9a3f04500aedf8440c45eadf8
Source dataset
uspto-grants-2009_12
Patent number
US07625905B2

Reaction notes

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