Hydrochloric Acid → HCID 58289879, compound

HRID 2036284Notes

Reaction equation

HRID 2036284 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[H-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[N:25]=[C:26]=[O:27].Cl>CN(C)C=O.C(OCC)(=O)C>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[N:25]1[C:8](=[O:10])[C:7]2[C:2](=[N:3][C:4]([S:13][CH3:14])=[N:5][CH:6]=2)[NH:1][C:26]1=[O:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2226665-Pyrimidinecarboxylic acid, 4-amino-2-(methylthio)-, ethyl esterHCID 6045371,3-Dichloro-2-isocyanatobenzene

Product 1

HCID 58289879HCID 58289879, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g of ethyl 4-amino-2-(methylsulfanyl)pyrimidine-5-carboxylate in 15 mL of N,N-dimethylformamide, 315 mg of sodium hydride was added, and the resulting mixture was stirred at room temperature for 5 minutes. To the reaction mixture, 970 mg of 2,6-dichlorophenyl isocyanate was added, and the resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture, ethyl acetate and a 1 N aqueous hydrochloric acid solution were added and the organic layer was separated. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate, and then, the solvent was distilled off. The precipitated solid was solidified with methanol and collected by filtration, whereby 1.43 g of the title compound was obtained as a white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1a967d4a4a5c44e49ee0bbbdd887753e
Source dataset
uspto-grants-2013_11
Patent number
US08575179B2

Reaction notes

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