23680-84-4

Basic information

• Product Name: 2-Chloro-4-amino-6,7-dimethoxyquinazoline
• Synonyms: QUINAZOLINAMINE;TIMTEC-BB SBB000787;4-Quinazolinamine, 2-chloro-6,7-dimethoxy-;4-AMINO-2-CHLORO-6,7-DIMETHOXYQUINAZOLINE;4-AMINO-2-CHLORO-6,7-DIMETHOXYQUINOZOLINE;4-AMINO-2-CHLORO-6,7-DIMETHOXY-QUINZOLINE;2-CHLORO-4-AMINO-6,7-DIMETHOXYQUINAZOLINE;2-CHLORO-6,7-DIMETHOXY-4-AMINOQUINAZOLINE
• CAS NO: 23680-84-4
• Molecular Formula: C₁₀H₁₀ClN₃O₂
• Molecular Weight: 239.66
• EINECS: 245-821-7
• Product Categories: Quinolines, Quinazolines and derivatives;BUILDING BLOCKS;Doxazosin;intermediate of terazosin);(intermediate of doxazosin);Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides;Alfuzosin Hydrochloride;Doxazosin Mesylate;Amines;Intermediates
• Mol File: 23680-84-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 262-268 °C (dec.)(lit.)
• Boiling Point: 374 °C at 760 mmHg
• Flash Point: 180 °C
• Appearance: off-white solid
• Density: 1.5062 (rough estimate)
• Vapor Pressure: 8.63E-06mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly, Heated), Methanol (Slightly, Heated)
• PKA: 4.35±0.30(Predicted)
• Water Solubility: 1.418g/L at 25℃
• BRN: 747463
• CAS DataBase Reference: 2-Chloro-4-amino-6,7-dimethoxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-amino-6,7-dimethoxyquinazoline(23680-84-4)
• EPA Substance Registry System: 2-Chloro-4-amino-6,7-dimethoxyquinazoline(23680-84-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 23680-84-4(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Intermediate in the production on Terazosin.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 20, p. 146, 1977 DOI: 10.1021/jm00211a031

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C10H10ClN3O2/c1-15-7-3-5-6(4-8(7)16-2)13-10(11)14-9(5)12/h3-4H,1-2H3,(H2,12,13,14)

Upstream product

• 68319-88-0 3-cyano-1-(3,4-dimethoxyphenyl)urea 
• 6315-89-5 3,4-dimethoxyaniline 
• 5004-88-6 4,5-dimethoxyanthranilamide 
• 4959-60-8 4,5-dimethoxy-2-nitrobenzamide 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 157459-53-5 3,4-dimethoxy-6-cyanoaniline-1-yl formamide 
• 607-68-1 2,4-dichloroquinazoline 
• 28888-44-0 6,7-dimethoxy-1H-quinazoline-2,4-dione 
• 28888-44-0 2,4-dihydroxy-6,7-dimethoxyquinazoline 
• 26759-46-6 methyl 2-amino-4,5-dimethoxybenzoate 
• 26791-93-5 methyl 4,5-dimethoxy-2-nitrobenzoate 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 192869-38-8 4-Amino-2-chloro-6,7-dimethoxy-5-iodoquinazoline 
• 81745-83-7 pyridin-2-ylzinc(ll) bromide 

Downstream Products

• 84050-18-0 4-amino-2-(4-cinnamoylpiperazino)-6,7-dimethoxyquinazoline hydrochloride 
• 766532-56-3 4-(4-amino-6,7-dimethoxy-quinazolin-2-yl)-piperazine-1-carboxylic acid benzyl ester 
• 141269-44-5 terazosin hydrochloride 
• 64579-66-4 4-Amino-2-[4-(3-cyclohexenylcarbonyl)-1-piperazinyl]-6,7-dimethoxyquinazoline 
• 75483-71-5 1-[1-(4-amino-6,7-dimethoxy-2:quinazolinyl)-4-piperidinyl]-3-methyl-3-phenyl-pyrrolidin-2,5-dione monomesylate 
• 104964-10-5 4-Amino-6,7-dimethoxy-2-(4-(5,6-dihydro-6-ethyl-5-oxopyrido[4,3-d]pyrimidin-2-yl)piperazino)quinazoline 
• 116728-65-5 1-(4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)-2-methoxypropan-1-one 

Relevant articles and documents

Zinc-mediated intramolecular acyl and imino transfer reactions of aryl iodides

A method for the coupling of acyl and imino substituents to the sterically encumbered 5-position of a 4-aminoquinazoline was developed. Starting with a 4-amino-5-iodoquinazoline, the method employs a facile intramolecular zinc-mediated transfer from the 4-amino group to the iodo-bearing carbon. The method was found to be effective for a variety of substituents, in particular a pyridyl group required for the synthesis of Pfizer's prostate selective α1 antagonist candidate for the treatment of benign prostatic hyperplasia, UK-338,003.

Synthetic method for 2-chloro-4-amino-6,7-dimethoxy quinazoline

The invention discloses a synthetic method for 2-chloro-4-amino-6,7-dimethoxy quinazoline. The synthetic method comprises the following steps: 1) preparing 3,4-dimethoxyphenyl isocyanate; 2) preparing 3,4-dimethoxyphenyl cyanourea; 3) preparing a 2-chloro-4-amino-6,7-dimethoxy quinazoline crude product; and 4) preparing a 2-chloro-4-amino-6,7-dimethoxy quinazoline fine product. The synthetic method disclosed by the invention simplifies reaction steps and increases the product yield; reaction conditions are optimized, so that reactants react more sufficiently, and therefore, generation of byproducts is reduced, production efficiency is improved, reactants are prevented from being oxidized, reaction is more complete, the target object can be obtained by direct filtering and drying during post-treatment, and the yield is stable.

Molecular features of the prazosin molecule required for activation of Transport-P

Closely related structural analogues of prazosin have been synthesised and tested for inhibition and activation of Transport-P in order to identify the structural features of the prazosin molecule that appear to be necessary for activation of Transport-P. So far, all the compounds tested are less active than prazosin. It is shown that the structure of prazosin appears to be very specific for the activation. Only quinazolines have been found to activate, and the presence of the 6,7-dimethoxy and 4-amino groups appears to be critically important.