Pyridine → 5-ethyl-N-(2-hydroxy-5-trifluoromethyl-phenyl)-pyrimidine-4-carboxamide

HRID 1527646Notes

Reaction equation

HRID 1527646 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[OH:12].[CH2:13]([C:15]1[C:16]([C:21](O)=[O:22])=[N:17][CH:18]=[N:19][CH:20]=1)[CH3:14].CCN=C=NCCCN(C)C.N1C=CC=CC=1>O>[CH2:13]([C:15]1[C:16]([C:21]([NH:1][C:2]2[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][C:3]=2[OH:12])=[O:22])=[N:17][CH:18]=[N:19][CH:20]=1)[CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1202462-Amino-4-(trifluoromethyl)phenolHCID 678120845-Ethylpyrimidine-4-carboxylic acid

Product 1

HCID 678123505-ethyl-N-(2-hydroxy-5-trifluoromethyl-phenyl)-pyrimidine-4-carboxamideYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-amino-4-trifluoromethyl-phenol (0.27 g), 5-ethyl-pyrimidine-4-carboxylic acid (0.27 g), WSC (0.25 g), and pyridine (5 ml) was stirred at 80° C. for 1 hour, at 100 for 1.5 hours, and at 115° C. for 0.5 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.34 g of 5-ethyl-N-(2-hydroxy-5-trifluoromethyl-phenyl)-pyrimidine-4-carboxamide.

Workup

  1. waitat 115° C. for 0.5 hours
  2. temperatureto cool the reaction mixture to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-46802a182200460bac1722ecba191705
Source dataset
uspto-grants-2015_07
Patent number
US09089136B2

Reaction notes

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