Sodium Hydroxide → HCID 178510347, compound

HRID 570004Notes

Reaction equation

HRID 570004 reaction equation
S(O)(O)(=O)=O.[C:6]([N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)(=[NH:8])[NH2:7].[OH-].[Na+].[C:24]([C:26](=[CH:32]OCC)[C:27](OCC)=[O:28])#[N:25]>C(O)C>[CH2:15]([N:12]1[CH2:13][CH2:14][N:9]([C:6]2[N:7]=[C:27]([OH:28])[C:26]([C:24]#[N:25])=[CH:32][N:8]=2)[CH2:10][CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl esterHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfate

Product 1

HCID 178510347HCID 178510347, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mixed were 26.8 g of 1-amidino-4-benzylpiperazine sulfate and 133 ml of a 3% ethanol solution of sodium hydroxide, followed by an addition of 17.0 g of ethyl 2-cyano-3-ethoxyacrylate. After being refluxed for 5 hours, the reaction mixture was allowed to cool down. After distilling off ethanol from the reaction mixture, the residue was added with water and ethyl acetate. The resultant mixture was shaken. Precipitated colorless crystals of 2-(4-benzylpiperazino)-5-cyano-4-hydroxypyrimidine were collected by filtration, washed with water and then dried, thereby obtaining 7.4 g of 2-(4-benzylpiperazino)-5-cyano-4-hydroxypyrimidine (yield: 25%).

Workup

  1. additionMixed
  2. temperatureAfter being refluxed for 5 hours
  3. temperatureto cool down
  4. distillationAfter distilling off ethanol from the reaction mixture
  5. additionthe residue was added with water and ethyl acetate
  6. customPrecipitated colorless crystals of 2-(4-benzylpiperazino)-5-cyano-4-hydroxypyrimidine
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-4e0ed297503a4f58a12092ce9108aa74
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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