(5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)

Base Information

• Chemical Name: (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)
• CAS No.: 330785-81-4
• Molecular Formula: C16H18 Cl N3 O3 S
• Molecular Weight: 367.856
• Hs Code.: 2933599090
• Mol file: 330785-81-4.mol

Synonyms:4-(3-Chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylthiopyrimidine

Chemical Property of (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)

Chemical Property:

• Boiling Point: 514.9±45.0 °C(Predicted)
• PKA: 2.70±0.10(Predicted)
• PSA: 101.87000
• Density: 1.33±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 3.07120
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

99%min ^*data from raw suppliers

4-(3-Chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylthiopyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(3-Chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylthiopyrimidine is an intermediate for Avanafil (A794670) derivatives. Avanafil is a phosphodiesterase (PDE5) inhibitor, used to treat erectile dysfunction.

Technology Process of (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)

There total 7 articles about (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl 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: 100.0%

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) + (3-chloro-4-methoxyphenyl)methanamine (115514-77-7) → ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate (330785-81-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2014.10.008 DOI:10.1016/j.bmcl.2015.02.041

Reference yield: 88.3%

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester (5909-24-0) + (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride (41965-95-1) → ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate (330785-81-4)

Guidance literature:

(3-chloro-4-methoxyphenyl)methylamine hydrogen chloride; With triethylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester; In tetrahydrofuran; at 20 ℃; Cooling with ice;

Reference yield:

ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate (53554-29-3) → ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate (330785-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate / toluene / 4 h / 55 - 105 °C

2: sodium carbonate / water / 4 h / 25 - 30 °C

With sodium carbonate; trichlorophosphate; In water; toluene;

upstream raw materials:

4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester

(3-chloro-4-methoxyphenyl)methanamine

4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylsulfinylpyrimidine

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

2-methylsulfonyl-5-ethoxycarbonyl-4-(3-chloro-4-methoxybenzylamino)pyrimidine

ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate

Refernces

• 1、 -. "Preparation method of avanafil". Paragraph 0027; 0031; 0036; 0040; 0045; 0049. . Retrieved 2018/11/22.
• 2、 -. "Atorvastatin that non-synthetic method". Paragraph 0025; 0050; 0051; 0052; 0053; 0054; 0055; 0056. . Retrieved 2017/08/25.