Sodium Hydroxide → HCID 136381437, compound

HRID 1907652Notes

Reaction equation

HRID 1907652 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].[OH-].[Na+].[N:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][C:16](OCC)=[O:17])=[N:10][CH:9]=1>C(O)C>[CH3:3][C:2]1[NH:4][C:16](=[O:17])[CH:15]=[C:14]([C:11]2[CH:12]=[CH:13][N:8]=[CH:9][N:10]=2)[N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67170Acetamidine monohydrochlorideHCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoate

Product 1

HCID 136381437HCID 136381437, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 200 g (2.11 mol) of acetamidine hydrochloride (1:1) in 1.2 L of ethanol were added 84 g (2.11 mol) of sodium hydroxide and 410 g (2.11 mol) of ethyl 3-(4-pyrimidinyl)-3-oxopropionate (prepared by analogy to the method described in patent DE 2705582). The resulting mixture was stirred under reflux for 12 h. The cooled solution was evaporated to remove solvent. The mixture was treated with water and the precipitate was filtered, washed with diethyl ether and ethyl acetate. The precipitate was stirred in a mixture of ethanol/water in the proportions 2/1 for 30 minutes to afford 200 g (50%) of the desired compound as a brown powder.

Workup

  1. customprepared by analogy to the method
  2. temperatureunder reflux for 12 h
  3. customThe cooled solution was evaporated
  4. customto remove solvent
  5. additionThe mixture was treated with water
  6. filtrationthe precipitate was filtered
  7. washwashed with diethyl ether and ethyl acetate
  8. stirringThe precipitate was stirred in a mixture of ethanol/water in the proportions 2/1 for 30 minutes

Sources & evidence

ORD record
ord-3cef89a530b443dfa78ff398da537a34
Source dataset
uspto-grants-2013_12
Patent number
US08598175B2

Reaction notes

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