Cyanogen Bromide → 2-(4-Cyanopiperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline

HRID 461329Notes

Reaction equation

HRID 461329 reaction equation
[N:1]1([C:7]2[N:16]=[C:15]([NH2:17])[C:14]3[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:22]#[C:23]Br>CN(C)C=O>[C:23]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:16]=[C:15]([NH2:17])[C:14]3[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=3)[N:8]=2)[CH2:2][CH2:3]1)#[N:22]

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g. (0.033 mole) of 2-(1-piperazinyl)-4-amino-6,7-dimethoxyquinazoline, prepared as described in U.S. Pat. No. 3,511,836, 3.54 g. (0.033 mole) of cyanogen bromide and 33 ml. of N,N-dimethylformamide was stirred under nitrogen at room temperature (20°-25° C.) for 6 hours. The precipitated solid was recovered by filtration, washed with ether and air dried to afford 11.6 g. (85%) of the hydrobromide salt of the title compound. The salt was partitioned between 250 ml. of aqueous saturated sodium bicarbonate solution and 500 ml. of chloroform. The layers were separated and the chloroform layer concentrated in vacuo to afford the free base as a dry foam, 8.3 g. (80%); M.P. 215° C. The mass spectrum reveals a molecular ion peak at M/e 314. Infrared spectrum (CHCl3): peak at 4.5 μ (CN).

Workup

  1. additionA mixture of 10.0 g
  2. filtrationThe precipitated solid was recovered by filtration
  3. washwashed with ether and air
  4. customdried
  5. customto afford 11.6 g

Sources & evidence

ORD record
ord-0707f2afef084eb4aca41fd75381d8c3
Source dataset
uspto-grants-1977_12
Patent number
US04062844

Reaction notes

Loading…