Potassium Hydroxide → HCID 178470707, compound

HRID 1032699Notes

Reaction equation

HRID 1032699 reaction equation
[OH-].[K+].S(O)(O)(=O)=O.[C:8]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)(=[NH:10])[NH2:9].[C:24]([CH:27]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:28](OCC)=[O:29])(=O)[CH3:25]>C(O)C.C1(C)C=CC=CC=1>[CH2:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[N:9]=[C:28]([OH:29])[C:27]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:24]([CH3:25])[N:10]=2)[CH2:12][CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 66197Butanedioic acid, 2-acetyl-, 1,4-diethyl esterHCID 27566524-Benzylpiperazine-1-carboxamidine hemisulfate

Product 1

HCID 178470707HCID 178470707, compoundYield 17.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

Potassium hydroxide (3.1 g) was added to 200 ml of ethanol, and the mixture was stirred for 30 minutes. Then, 12.4 g of 1-amidino-4-benzylpiperazine sulfate was added. The mixture was stirred at room temperature for 10 minutes. To the solution was added 12.4 g of diethyl acetylsuccinate. The mixture was refluxed for 2 hours. Then, 200 ml of toluene was added, and the mixture was refluxed for 3 hours. After the reaction, ethanol was evaporated, and the residue was poured into 50 ml of an aqueous solution of hydrochloric acid. NaHCO3 was added to the solution to neutralize it. The precipitated solid was washed with water and dried over P2O5 to give 2.55 g (yield 15%) of 2-(4-benzylpiperazino)-5-ethoxycarbonylmethyl-4-hydroxy-6-methylpyrimidine as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 minutes
  2. temperatureThe mixture was refluxed for 2 hours
  3. temperaturethe mixture was refluxed for 3 hours
  4. customwas evaporated
  5. additionthe residue was poured into 50 ml of an aqueous solution of hydrochloric acid
  6. additionNaHCO3 was added to the solution
  7. washThe precipitated solid was washed with water
  8. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-6eeed99592f143d0b3ed66f071cf2705
Source dataset
uspto-grants-1990_09
Patent number
US04959368

Reaction notes

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