Ethanol → 4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)piperazine-1-imidic Acid Ethyl Ester

HRID 461333Notes

Reaction equation

HRID 461333 reaction equation
[CH2:1]([OH:3])[CH3:2].[Na].[C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:22]=[C:21]([NH2:23])[C:20]3[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([O:24][CH3:25])[CH:19]=3)[N:14]=2)[CH2:9][CH2:8]1)#[N:6]>C(O)(=O)C>[CH2:1]([O:3][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:22]=[C:21]([NH2:23])[C:20]3[C:15](=[CH:16][C:17]([O:26][CH3:27])=[C:18]([O:24][CH3:25])[CH:19]=3)[N:14]=2)[CH2:9][CH2:8]1)=[NH:6])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 5360545Sodium2×HCID 213933662-(4-Cyanopiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 541908694-(4-Amino-6,7-dimethoxyquinazolin-2-yl)piperazine-1-imidic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a dry flask equipped with stirrer, thermometer and reflux condenser is placed 25 ml. of ethanol and sodium metal, 0.253 g. (0.011 g. atom) is added in portions. When the sodium is completely reacted, 3.14 g. (0.01 mole) of 2-(4-cyanopiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline is added and the resulting mixture is refluxed for 5 hours. After cooling to room temperature, glacial acetic acid is added to neutralize the mixture. After evaporation to dryness, 25 ml. of water and 50 ml. of chloroform are added to the residue. The mixture is transferred to a separatory funnel and the chloroform layer washed again with water, dried over anhydrous sodium sulfate then concentrated to dryness to provide the title compound.

Workup

  1. customTo a dry flask equipped with stirrer
  2. temperaturethermometer and reflux condenser
  3. addition(0.011 g. atom) is added in portions
  4. temperaturethe resulting mixture is refluxed for 5 hours
  5. customAfter evaporation to dryness, 25 ml
  6. additionof chloroform are added to the residue
  7. customThe mixture is transferred to a separatory funnel
  8. washthe chloroform layer washed again with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationthen concentrated to dryness

Sources & evidence

ORD record
ord-48208be7e38f41ac839ecf78dbd7004c
Source dataset
uspto-grants-1977_12
Patent number
US04062844

Reaction notes

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