Hydrochloric Acid → HCID 58289879, compound

HRID 2088748Notes

Reaction equation

HRID 2088748 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([C:10]([O:12]CC)=O)=[CH:8][N:7]=[C:6]([S:15][CH3:16])[N:5]=1.[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>C(OCC)(=O)C.CN(C)C=O>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[N:25]1[C:10](=[O:12])[C:9]2[C:4](=[N:5][C:6]([S:15][CH3:16])=[N:7][CH:8]=2)[NH:3][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

315 mg of sodium hydride was added to an N,N-dimethylformamide (15 mL) solution of 1.0 g of ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate, and stirred at room temperature for 5 minutes. 970 mg of 2,6-dichlorophenylisocyanate was added to the reaction liquid, and stirred at room temperature for 1 hour. Ethyl acetate and aqueous 1 N hydrochloric acid solution were added to the reaction solution, and the organic layer was separated. This was washed with saturated saline water, dried with anhydrous sodium sulfate, and the solvent was evaporated away. The precipitated solid was solidified with methanol, and the solid was taken out through filtration to obtain 1.43 g of the entitled compound as a white solid.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. washThis was washed with saturated saline water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was evaporated away
  6. filtrationthe solid was taken out through filtration

Sources & evidence

ORD record
ord-3084eec47ae74bd9a1ce600351f50920
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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