4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester

Base Information

• Chemical Name: 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester
• CAS No.: 917392-54-2
• Molecular Formula: C18H16 N4 O2
• Molecular Weight: 320.351
• Hs Code.: 2916399090
• Mol file: 917392-54-2.mol

Synonyms:methyl 4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzoate;

Chemical Property of 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 148 - 150°C
• Boiling Point: 538.59oC at 760 mmHg
• PKA: 2.70±0.12(Predicted)
• Flash Point: 279.53oC
• PSA: 77.00000
• Density: 1.258
• LogP: 3.45020
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-Methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 4-methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate is an intermediate used in the synthesis of 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzamide (M326838), which is an impurity of Nilotinib (N465300), a possible agent in the treatment of chronic myelogenous leukemia.

Technology Process of 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester

There total 12 articles about 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid methyl ester 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: 95.0%

methyl 3-bromo-4-methylbenzoate (104901-43-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate (917392-54-2)

Guidance literature:

With C₄₃H₆₃ClNO₂PPd; caesium carbonate; In 1,4-dioxane; at 120 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ja2102373

Reference yield: 86.0%

3-amino-4-methyl benzoic acid methyl ester (18595-18-1) + 2-chloro-4-(pyridin-3-yl)pyrimidine (483324-01-2) → methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate (917392-54-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100 ℃; Inert atmosphere;

Reference yield: 81.0%

methyl 3-iodo-4-methylbenzoate (90347-66-3) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate (917392-54-2)

Guidance literature:

With copper(l) iodide; potassium carbonate; In 1,4-dioxane; at 20 - 120 ℃; Sealed tube; Inert atmosphere;

DOI:10.1039/b913333j

upstream raw materials:

3-[(aminoiminomethyl)amino]-4-methylbenzoic acid methylester mononitrate

(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

3-guanidino-4-methylbenzoic acid methyl ester

Downstream raw materials:

4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid

nilotinib

N-(3-bromo-5-(trifluoromethyl)phenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide

4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid N'-4-[[(4-methyl-1-piperazinyl)methyl]benzoyl]hydrazide

Refernces

• 1、 -. "MANUFACTURING METHOD OF BENZOIC ACID COMPOUND". . . Retrieved 2020/02/18.
• 2、 Li, Yong-Tao,Wang, Jing-Han,Pan, Cheng-Wen,Meng, Fan-Fei,Chu, Xiao-Qian,Ding, Ya-Hui,Qu, Wen-Zheng,Li, Hui-Ying,Yang, Cheng,Zhang, Quan,Bai, Cui-Gai,Chen, Yue. "Syntheses and biological evaluation of 1,2,3-triazole and 1,3,4-oxadiazole derivatives of imatinib". . p. 1419 - 1427. Retrieved 2016/02/19.