Potassium Hydroxide → HCID 178525223, compound

HRID 1032694Notes

Reaction equation

HRID 1032694 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[C:18]([OH:20])[C:17]([CH2:21][C:22]([O:24]CC)=[O:23])=[CH:16][N:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:19]=[C:18]([OH:20])[C:17]([CH2:21][C:22]([OH:24])=[O:23])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178470734Ethyl 2-(4-benzylpiperazino)-4-hydroxypyrimidine-5-acetate

Product 1

HCID 178525223HCID 178525223, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture composed of 20 g (56.1 mmoles) of ethyl 2-(4-benzylpiperazino)-4-hydroxypyrimidine-5-acetate (prepared in accordance with Referential Example 70 of Japanese Laid-Open Patent Publication No. 140568/1986), 7.5 g (114 moles) of 85% KOH tablets and 320 ml of ethanol was refluxed for 1 hour. The reaction mixture was concentrated to a solid. Hydrochloric acid and saturated aqueous sodium bicarbonate solution were added to adjust the pH to 4, and the mixture was again concentrated. The resulting crude crystals were recrystallized from water to give 17 g (yield 92%) of 2-(4-benzylpiperazino)-4-hydroxypyrimidine-5-acetic acid as a colorless solid.

Workup

  1. customprepared in accordance with Referential Example 70 of Japanese Laid-Open Patent Publication No
  2. concentrationThe reaction mixture was concentrated to a solid
  3. additionHydrochloric acid and saturated aqueous sodium bicarbonate solution were added
  4. concentrationthe mixture was again concentrated
  5. customThe resulting crude crystals were recrystallized from water

Sources & evidence

ORD record
ord-da4641c3adab4b78b1731b1683f98904
Source dataset
uspto-grants-1990_09
Patent number
US04959368

Reaction notes

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