Sodium Hydroxide → 2-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

HRID 1414237Notes

Reaction equation

HRID 1414237 reaction equation
Br.[NH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[C:11](Cl)[N:10]=1.[OH-].[Na+]>COCCO.O>[NH2:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12]=[C:11]([N:2]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)[N:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 3014804Piperazine--hydrogen bromide (1/1)

Product 1

HCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
75 °C

Procedure

Piperazine hydrobromide (168.0 g., 1.006 mole) was added to a suspension of 4-amino-2-chloro-6,7-dimethoxyquinazoline (241.0 g., 1.006 mole) in 2-methoxyethanol (3.6 l.) and the mixture was stirred at reflux for 1.25 hours. The precipitate was separated by filtration, washed with hot 2-methoxyethanol and dried. The material then was added to a stirred solution of sodium hydroxide (81.0 g., 2.01 mole) in water (3 l.) and the mixture was heated to 75° C. The mixture then was cooled to 40° C., filtered, and the insoluble precipitate washed with water and dried. The material was triturated under refluxing absolute ethanol (6.0 l.) and the mixture was filtered. The filtrate was evaporated to dryness to yield the title compound, 180.0 g. (62%), M.P. 224°-228° C.

Workup

  1. temperatureat reflux for 1.25 hours
  2. customThe precipitate was separated by filtration
  3. washwashed with hot 2-methoxyethanol
  4. customdried
  5. temperatureThe mixture then was cooled to 40° C.
  6. filtrationfiltered
  7. washthe insoluble precipitate washed with water
  8. customdried
  9. customThe material was triturated
  10. temperatureunder refluxing absolute ethanol (6.0 l.)
  11. filtrationthe mixture was filtered
  12. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-c8156cdc59b7426ba17db8c58dbc4bca
Source dataset
uspto-grants-1977_01
Patent number
US04001238

Reaction notes

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