Hydrochloric Acid → HCID 58458121, compound

HRID 2036285Notes

Reaction equation

HRID 2036285 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]([CH3:24])[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]([CH3:24])[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 2681232-Chloro-6-methylphenyl isocyanate

Product 1

HCID 58458121HCID 58458121, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 100 mg of ethyl 4-amino-2-(methylsulfanyl)pyrimidine-5-carboxylate in 4 mL of N,N-dimethylformamide, 56 mg of sodium hydride was added, and the resulting mixture was stirred at room temperature for 5 minutes. To the reaction mixture, 118 mg of 2-chloro-6-methylphenyl 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 100 mg 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-ff82b492940e4440aedaab102cd6c68f
Source dataset
uspto-grants-2013_11
Patent number
US08575179B2

Reaction notes

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