Sodium Hydroxide → HCID 136375845, compound

HRID 1907864Notes

Reaction equation

HRID 1907864 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:17])[NH:11][CH2:12][CH2:13][C:14](=[NH:16])[NH2:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+].[N:20]1[CH:25]=[CH:24][C:23]([C:26](=O)[CH2:27][C:28](OCC)=[O:29])=[N:22][CH:21]=1>C(O)C>[CH2:2]([O:9][C:10](=[O:17])[NH:11][CH2:12][CH2:13][C:14]1[NH:15][C:28](=[O:29])[CH:27]=[C:26]([C:23]2[CH:24]=[CH:25][N:20]=[CH:21][N:22]=2)[N:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoateHCID 68577815HCID 68577815, compound

Product 1

HCID 136375845HCID 136375845, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6 g (23.3 mmol) of (2-Carbamimidoyl-ethyl)-carbamic acid benzyl ester hydrochloride (1:1) in 60 ml of ethanol were added 0.93 g (23.3 mmol) of sodium hydroxide and 4.5 g (23.3 mmol) of ethyl 3-(4-pyrimidinyl)-3-oxopropionate (prepared by analogy to the method described in patent DE2705582). The resulting mixture was stirred under reflux for 12 h. The cooled solution was evaporated to remove solvent. The resulting mixture was treated with water and the precipitate was filtered, washed with diethyl ether to afford 2.7 g (33%) 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 resulting mixture was treated with water
  6. filtrationthe precipitate was filtered
  7. washwashed with diethyl ether

Sources & evidence

ORD record
ord-3aee21ffa165466e88bf8d7f4d21e29c
Source dataset
uspto-grants-2013_12
Patent number
US08598187B2

Reaction notes

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