Potassium Hydroxide → 2-(4-Cyanopiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

HRID 461330Notes

Reaction equation

HRID 461330 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4](Br)[N:3]=1.[C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)#[N:18].[OH-].[K+]>>[C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:4]2[N:3]=[C:2]([NH2:1])[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=2)[CH2:21][CH2:20]1)#[N:18]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 203205122-Bromo-6,7-dimethoxyquinazolin-4-amineHCID 22633091Piperazine-1-carbonitrile

Product 1

HCID 213933662-(4-Cyanopiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

Procedure

In a flask fitted with stirrer, thermometer, and drying tube is placed 100 ml. of chloroform, 12.0 g. (0.05 mole) of 4-amino-2-bromo-6,7-dimethoxyquinazoline (prepared by the method of U.S. Pat. No. 3,511,836) and 5.8 g. (0.052 mole) of 1-cyanopiperazine. The mixture is maintained at 50° C. for 24 hours after which 2N potassium hydroxide solution is added at room temperature to adjust to pH 9.5. The organic layer is separated and the aqueous phase extracted again with chloroform and the combined extracts are evaporated to dryness to obtain 2-(4-cyanopiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline.

Workup

  1. customIn a flask fitted with stirrer
  2. customthermometer, and drying tube
  3. additionis added at room temperature
  4. customThe organic layer is separated
  5. extractionthe aqueous phase extracted again with chloroform
  6. customthe combined extracts are evaporated to dryness

Sources & evidence

ORD record
ord-610d6ab3dd524579bd5a158c02a818e0
Source dataset
uspto-grants-1977_12
Patent number
US04062844

Reaction notes

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