21575-13-3

Basic information

• Product Name: 4-Amino-6,7-dimethoxyquinazoline
• Synonyms: 4-AMINO-6,7-DIMETHOXYQUINAZOLINE;6,7-Dimethoxy-4-Amino-Quinzaoline;6,7-DiMethoxy-4-quinazolinaMine;6,7-diMethoxyquinazolin-4-aMine;6,7-Dimethoxy-quinazolin-4-ylamine
• CAS NO: 21575-13-3
• Molecular Formula: C₁₀H₁₁N₃O₂
• Molecular Weight: 205.21
• EINECS: 1533716-785-6
• Product Categories: Tinibs
• Mol File: 21575-13-3.mol

Chemical Properties

• Boiling Point: 383.053 °C at 760 mmHg
• Flash Point: 185.464 °C
• Appearance: /
• Density: 1.28 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.642
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 4-Amino-6,7-dimethoxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-6,7-dimethoxyquinazoline(21575-13-3)
• EPA Substance Registry System: 4-Amino-6,7-dimethoxyquinazoline(21575-13-3)

Safety Data

• Hazardous Substances Data: 21575-13-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Amino-6,7-dimethoxyquinazoline is used as a key intermediate in the synthesis of various pharmaceutical drugs. Its versatile chemical structure allows for the development of new drug candidates with potential therapeutic applications.
Used in Anticancer Applications:
4-Amino-6,7-dimethoxyquinazoline is used as an anti-cancer agent for its potential to target and inhibit the growth of cancer cells. Its biological activities have been studied, and it has shown promise in the treatment of various types of cancer.
Used in Anti-inflammatory Applications:
4-Amino-6,7-dimethoxyquinazoline is used as an anti-inflammatory agent due to its potential to reduce inflammation and alleviate symptoms associated with inflammatory conditions.
Used in Anti-fibrotic Applications:
4-Amino-6,7-dimethoxyquinazoline is used as an anti-fibrotic agent for its potential to prevent or reduce the formation of fibrous tissue, which can be beneficial in the treatment of fibrosis-related diseases.
Used in Neurodegenerative Disease Treatment:
4-Amino-6,7-dimethoxyquinazoline is used in the research and development of treatments for neurodegenerative diseases, given its potential to target and mitigate the progression of such conditions.

InChI:InChI=1/C10H11N3O2/c1-14-8-3-6-7(4-9(8)15-2)12-5-13-10(6)11/h3-5H,1-2H3,(H2,11,12,13)

Upstream product

• 26961-27-3 2-amino-4,5-dimethoxybenzonitrile 
• 77287-34-4 formamide 
• 3473-63-0 formamidine acetic acid 
• 13790-39-1 6,7-dimethoxy-4-chloroquinazoline 
• 109305-98-8 2-bromo-4,5-dimethoxybenzonitrile 
• 6313-33-3 formamidine hydrochloride 

Downstream Products

• 1352198-29-8 N-[4,5-dimethoxy-2-([1,2,4]oxadiazol-5-yl)phenyl]formamide oxime 
• 1352198-55-0 N-[4,5-dimethoxy-2-(3-methyl[1,2,4]oxadiazol-5-yl)phenyl]formamide oxime 
• 1418025-25-8 7-chloro-3-[(6,7-dimethoxy-quinazolin-4-ylamino)methyl]-1-phenyl-1H-quinolin-4-one 

Relevant articles and documents

Synthetic method of erlotinib intermediate

The invention relates to a synthesis method of an erlotinib intermediate, which comprises the following steps: reacting 2-bromo-4,5-dimethoxybenzonitrile with formamidine hydrochloride under the actions of alkali and a catalyst to generate a compound 3; reacting with 1-bromo-triethynylbenzene under the catalysis of alkali to generate a compound 2; carrying out a reaction on the compound 2 with 48%hydrobromic acid under the action of a catalyst to obtain a compound 1. The method is mild in condition, simple in step, safe, environmentally friendly and suitable for industrial production.

Discovery and optimization of 1-(4-chloro-3-(trifluoromethyl)-phenyl)-3-(2-(amino)pyridin-3-yl)ureas as novel kdr kinase inhibitors

Kinase insert Domain-containing Receptor (KDR) is one of the currently validated targets for anticancer drug discovery and development. Herein, a series of o-amino-arylurea derivatives have been synthesized and evaluated for their kinase inhibitory activity. The optimization on the basis of biological screening and molecular modeling resulted in obvious increase in KDR kinase inhibitory activity compared with the hit compound. Eventually, we identified a potent inhibitor 5a of 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-((quinolin-4-ylmethyl) amino)pyridin-3-yl)urea scaffold against KDR (IC50 = 0.0689 μM), which can serve as good starting point for further KDR inhibitor optimization and development.

Discovery and Optimization of 1-(4-chloro-3-(trifluoromethyl)-phenyl)-3-(2-(amino)pyridin-3-yl)ureas as Novel KDR Kinase Inhibitors

Kinase insert Domain-containing Receptor (KDR) is one of the currently validated targets for anticancer drug discovery and development. Herein, a series of o-amino-arylurea derivatives have been synthesized and evaluated for their kinase inhibitory activity. The optimization on the basis of biological screening and molecular modeling resulted in obvious increase in KDR kinase inhibitory activity compared with the hit compound. Eventually, we identified a potent inhibitor 5a of 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-((quinolin-4-ylmethyl) amino)pyridin-3-yl)urea scaffold against KDR (IC50 = 0.0689 μM), which can serve as good starting point for further KDR inhibitor optimization and development.

Mild and highly selective palladium-catalyzed monoarylation of ammonia enabled by the use of bulky biarylphosphine ligands and palladacycle precatalysts

A method for the Pd-catalyzed arylation of ammonia with a wide range of aryl and heteroaryl halides, including challenging five-membered heterocyclic substrates, is described. Excellent selectivity for monoarylation of ammonia to primary arylamines was achieved under mild conditions or at rt by the use of bulky biarylphosphine ligands (L6, L7, and L4) as well as their corresponding aminobiphenyl palladacycle precatalysts (3a, 3b, and 3c). As this process requires neither the use of a glovebox nor high pressures of ammonia, it should be widely applicable.

Polycyclic N-heterocyclic compounds, part 67: Reaction of 6,7-substituted N-(quinazolin-4-yl)amidine derivatives with hydroxylamine hydrochloride: Formation of in vitro inhibitors of pentosidine

Reactions of N-(quinazolin-4-yl)amidines and their amide oximes with hydroxylamine hydrochloride gave cyclization products that were formed by an initial ring cleavage of the pyrimidine component followed by a ring closure formation of 1,2,4-oxadiazole to

Microwave-assisted thermal decomposition of formamide: A tool for coupling a pyrimidine ring with an aromatic partner

Rapid and efficient generation of CO and NH3 in the reaction mixture via microwave-assisted thermal decomposition of formamide may represent a significant improvement over existing methods for coupling a pyrimidine ring with an aromatic partner. This work aims at alerting readers on the probability to observe interesting phenomena and reactions when this very powerful heating mode is associated with thermally unstable reagents.