1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67812272, compound

HRID 1527645Notes

Reaction equation

HRID 1527645 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.CCN=C=NCCCN(C)C.[Cl:25][C:26]1[C:27]([C:32](O)=[O:33])=[N:28][CH:29]=[N:30][CH:31]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C1COCC1>[Cl:25][C:26]1[C:27]([C:32]([NH:9][C:8]2[C:3]([NH:2][CH3:1])=[N:4][CH:5]=[C:6]([C:10]([F:13])([F:11])[F:12])[CH:7]=2)=[O:33])=[N:28][CH:29]=[N:30][CH:31]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516892Sodium BicarbonateHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 200293965-Chloropyrimidine-4-carboxylic acid

Product 1

HCID 67812272HCID 67812272, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of N2-methyl-5-trifluoromethylpyridine-2,3-diamine (2.65 g), WSC (2.66 g), 4-dimethylaminopyridine (0.10 g), THF (10 ml), and pyridine (10 ml), 5-chloropyrimidine-4-carboxylic acid was added under ice-cooling, and the reaction mixture was stirred at 50° C. for 8 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 1.77 g of 5-chloro-N-(2-methylamino-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-39b89df4634f45a0b29e8ffcfe96b84b
Source dataset
uspto-grants-2015_07
Patent number
US09089136B2

Reaction notes

Loading…