1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178437155, compound

HRID 1527644Notes

Reaction equation

HRID 1527644 reaction equation
[NH2:1][C:2]1[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CCN=C=NCCCN(C)C.[CH2:24]([C:26]1[C:27]([C:32](O)=[O:33])=[N:28][CH:29]=[N:30][CH:31]=1)[CH3:25].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[CH2:24]([C:26]1[C:27]([C:32]([NH:1][C:2]2[C:3]([OH:12])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=2)=[O:33])=[N:28][CH:29]=[N:30][CH:31]=1)[CH3:25]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 23157873-Amino-5-(trifluoromethyl)-1,2-dihydropyridin-2-oneHCID 678120845-Ethylpyrimidine-4-carboxylic acid

Product 1

HCID 178437155HCID 178437155, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 3-amino-5-trifluoromethylpyridin-2-ol (0.27 g), WSC (0.58 g), and pyridine (10 ml), 5-ethyl-pyrimidine-4-carboxylic acid was added under ice-cooling, and the reaction mixture was stirred at 80° C. for 10 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.26 g of 5-ethyl-N-(2-hydroxy-5-trifluoromethyl-pyridin-3-yl)-pyrimidine-4-carboxamide.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperatureto cool the reaction mixture to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd1fe6254efa4c7bb9843e2c96d8a663
Source dataset
uspto-grants-2015_07
Patent number
US09089136B2

Reaction notes

Loading…