2-Chloro-6,7-dimethoxy-4-quinazolinamine → 2-{4-[3-(Furan-2-yl)-acryloyl]-piperazin-1-yl}-4-amino-6,7-dimethoxyquinazoline

HRID 1449161Notes

Reaction equation

HRID 1449161 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH:22]=[CH:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25]>C(O)CC(C)C>[O:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[CH:22]=[CH:23][C:24]([N:26]1[CH2:27][CH2:28][N:29]([C:2]2[N:11]=[C:10]([NH2:12])[C:9]3[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=3)[N:3]=2)[CH2:30][CH2:31]1)=[O:25]

Participants

4

Reactant 2

HCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 537585833-(Furan-2-yl)-acryloylpiperazine

Product 1

HCID 541791452-{4-[3-(Furan-2-yl)-acryloyl]-piperazin-1-yl}-4-amino-6,7-dimethoxyquinazoline

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 479 mg. (2 mM) of 2-chloro-4-amino-6,7-dimethoxyquinazoline and 412 mg. (2 mM) of 3-(furan-2-yl)-acryloylpiperazine in 10 ml. of isoamyl alcohol was heated under reflux for 4 hours. After ice-cooling, the crystalline substance thus separated was recovered by filtration and washed with ethanol to afford 685 mg. of the desired product as the hydrochloride.

Workup

  1. additionA mixture of 479 mg
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter ice-cooling
  4. customthe crystalline substance thus separated
  5. filtrationwas recovered by filtration
  6. washwashed with ethanol
  7. customto afford 685 mg

Sources & evidence

ORD record
ord-94eca3ef45e244e4ac3a3b90588c28b8
Source dataset
uspto-grants-1980_02
Patent number
US04189484

Reaction notes

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