4-Amino-2-chloro-6,7-dimethoxyquinazoline

Base Information

• Chemical Name: 4-Amino-2-chloro-6,7-dimethoxyquinazoline
• CAS No.: 23680-84-4
• Molecular Formula: C10H10ClN3O2
• Molecular Weight: 239.661
• Hs Code.: 29339900
• European Community (EC) Number: 245-821-7
• UNII: FG7Z4T71Y4
• DSSTox Substance ID: DTXSID3057694
• Nikkaji Number: J86.521D
• Wikidata: Q27277971
• ChEMBL ID: CHEMBL3561187
• Mol file: 23680-84-4.mol

Synonyms:23680-84-4;4-Amino-2-chloro-6,7-dimethoxyquinazoline;2-Chloro-6,7-dimethoxyquinazolin-4-amine;2-Chloro-4-amino-6,7-dimethoxyquinazoline;2-Chloro-6,7-dimethoxy-4-quinazolinamine;4-Quinazolinamine, 2-chloro-6,7-dimethoxy-;2680-84-4;MFCD00051734;UNII-FG7Z4T71Y4;FG7Z4T71Y4;2-chloro-4-amino-6,7-dimethoxy quinazoline;2-chloro-4-amino-6,7-dimethoxy-quinazoline;DTXSID3057694;EINECS 245-821-7;EC 245-821-7;SR-01000197509;Prazosin impurity A;Doxazosin impurity F;Terazosin impurity A;BIDD:GT0452;SCHEMBL611438;10-PROPOXY-DECANOICACID;CHEMBL3561187;DTXCID4031483;(E/Z)-Trelnarizine Dihydrochloride;BCP28790;Tox21_113801;STK503641;AKOS000264944;AC-5334;PS-3289;4amino-2-chloro6,7-dimethoxyquinazoline;NCGC00253677-01;4-amino-2chloro-6,7-dimethoxyquinazoline;SY008892;4-AMino-2-chloro-6,7-diMethoxyquinazolin;2-chloro-6,7-dimethoxy quinazolin-4-amine;2-chloro-6,7-dimethoxy-4-aminoquinazoline;2-chloro-6,7-dimethoxyquinazolin-4-ylamine;4-amino-2chloro-6,7-dimethoxy quinazoline;CAS-23680-84-4;2-chloro-4-amino-6,7-dimethoxyquin-azoline;2-Chloro-6,7-dimethoxy-4-quinazolinamine #;4-Amino-2-chloro-6,7-bismethoxyquinazoline;4-amino-2-chloro-6,7-dimethoxy quinazoline;4-amino-2-chloro-6,7-dimethoxy-quinazoline;AM20030412;BB 0257419;CS-0127991;FT-0620860;EN300-66004;4-Amino-2-chloro-6,7-dimethoxyquinazoline, 95%;AE-848/31926053;DOXAZOSIN MESILATE IMPURITY F [EP IMPURITY];SR-01000197509-1;SR-01000197509-2;W-107385;PRAZOSIN HYDROCHLORIDE IMPURITY A [EP IMPURITY];Q27277971;QUINAZOLINE, 4-AMINO-2-CHLORO-6,7-DIMETHOXY-;ALFUZOSIN HYDROCHLORIDE IMPURITY B [EP IMPURITY];Z1033088242;Doxazosin impurity F, European Pharmacopoeia (EP) Reference Standard;TERAZOSIN HYDROCHLORIDE DIHYDRATE IMPURITY A [EP IMPURITY];Terazosin impurity A, European Pharmacopoeia (EP) Reference Standard;4-Amino-2-chloro-6,7-dimethoxyquinazoline, puriss., >=99.0% (HPLC)

Chemical Property of 4-Amino-2-chloro-6,7-dimethoxyquinazoline

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 8.63E-06mmHg at 25°C
• Melting Point: 262-268 °C (dec.)(lit.)
• Refractive Index: 1.649
• Boiling Point: 374 °C at 760 mmHg
• PKA: 4.35±0.30(Predicted)
• Flash Point: 180 °C
• PSA: 70.26000
• Density: 1.391 g/cm³
• LogP: 2.46380
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly, Heated), Methanol (Slightly, Heated)
• Water Solubility.: 1.418g/L at 25℃
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 239.0461543
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-2-chloro-6,7-dimethoxyquinazoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C2C(=C1)C(=NC(=N2)Cl)N)OC
• Uses: Intermediate in the production on Terazosin.

Technology Process of 4-Amino-2-chloro-6,7-dimethoxyquinazoline

There total 16 articles about 4-Amino-2-chloro-6,7-dimethoxyquinazoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

3,4-dimethoxy-6-cyanoaniline-1-yl formamide (157459-53-5) → 2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4)

Guidance literature:

With trichlorophosphate; at 25 - 70 ℃; for 1h;

Reference yield: 68.0%

2-chloro-6,7-dimethoxy-3H-quinazolin-4-one (27631-29-4) → 2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4)

Guidance literature:

With ammonia; In tetrahydrofuran; at 20 ℃; for 44h;

DOI:10.1021/jo026217o

Reference yield:

3-cyano-1-(3,4-dimethoxyphenyl)urea (68319-88-0) → 2-chloro-6,7-dimethoxyquinazolin-4-amine (23680-84-4)

Guidance literature:

3-cyano-1-(3,4-dimethoxyphenyl)urea; With phosphorus pentachloride; trichlorophosphate; In water; toluene; at 10 ℃; for 3.5h; Reflux;

With formic acid; In water; toluene; for 0.5h; Reflux;

With triethylamine; In ethanol; for 0.5h; Reflux;

upstream raw materials:

2-chloro-6,7-dimethoxy-3H-quinazolin-4-one

pyridin-2-ylzinc(ll) bromide

4-Amino-2-chloro-6,7-dimethoxy-5-iodoquinazoline

methyl 3,4-dimethoxybenzoate

Downstream raw materials:

4-amino-6,7-dimethoxy-2-(4-formylpiperazino)quinazoline hydrochloride

6,7-dimethoxy-2-(1-phenyl-3-thiosemicarbazido)-4-aminoquinazoline

N-[3-(4-Amino-6,7-dimethoxy-quinazolin-2-ylamino)-propyl]-benzamide; hydrochloride

N²-[2-(2,6-Dimethoxy-phenoxy)-ethyl]-6,7-dimethoxy-N²-methyl-quinazoline-2,4-diamine

Refernces

• 1、 Mizukawa, Yuki,Ikegami-Kawai, Mayumi,Horiuchi, Masako,Kaiser, Marcel,Kojima, Masayoshi,Sakanoue, Seiki,Miyagi, Seiya,Nanga Chick, Christian,Togashi, Hiroyuki,Tsubuki, Masayoshi,Ihara, Masataka,Usuki, Toyonobu,Itoh, Isamu. "Quest for a potent antimalarial drug lead: Synthesis and evaluation of 6,7-dimethoxyquinazoline-2,4-diamines". . . Retrieved 2021/02/03.
• 2、 Yadav,Naik,Gandhi,Chauhan,Giridhar. "Design and synthesis of 6,7-dimethoxyquinazoline analogs as multi-targeted ligands for α1- and AII-receptors antagonism". . p. 3959 - 3966. Retrieved 2013/07/27.