5-PyriMidinecarboxylic acid,4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)-1-pyrrolidinyl]-, ethyl ester

Base Information

• Chemical Name: 5-PyriMidinecarboxylic acid,4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)-1-pyrrolidinyl]-, ethyl ester
• CAS No.: 330785-83-6
• Molecular Formula: C20H25ClN4O4
• Molecular Weight: 420.89000
• Mol file: 330785-83-6.mol

Synonyms:

Chemical Property of 5-PyriMidinecarboxylic acid,4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)-1-pyrrolidinyl]-, ethyl ester

Chemical Property:

• Boiling Point: 607.5±65.0 °C(Predicted)
• PKA: 14.77±0.10(Predicted)
• PSA: 100.04000
• Density: 1.317±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 2.37540
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99%min ^*data from raw suppliers

(S)-Ethyl4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-Ethyl 4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylate is an avanafil related compound. Avanafil (A794670 ) is a potent and highly selective phosphodiesterase 5 inhibitor use in the treatment of erectile dysfunction.

Technology Process of 5-PyriMidinecarboxylic acid,4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)-1-pyrrolidinyl]-, ethyl ester

There total 28 articles about 5-PyriMidinecarboxylic acid,4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)-1-pyrrolidinyl]-, 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%

2-chloro-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine (330786-00-0) + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate (1638497-22-9,330785-83-6)

Guidance literature:

at 20 ℃;

DOI:10.1016/j.bmcl.2014.10.008

Reference yield: 98.0%

2-methylsulfonyl-5-ethoxycarbonyl-4-(3-chloro-4-methoxybenzylamino)pyrimidine (372117-76-5) + (S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) → ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate (1638497-22-9,330785-83-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; Reagent/catalyst; Temperature;

Reference yield: 93.1%

ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate (330785-81-4) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate (1638497-22-9,330785-83-6)

Guidance literature:

In dimethyl sulfoxide; at 100 - 130 ℃; for 0.3h; Concentration; Solvent; Microwave irradiation;

upstream raw materials:

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

(S)-1-Pyrrolidin-2-yl-methanol

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

ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate

Downstream raw materials:

avanafil

Refernces

• 1、 -. "Preparation method of avanafil impurity". Paragraph 0031; 0034; 0044-0049. . Retrieved 2021/05/19.
• 2、 -. "A arab league cuts down that non-intermediate the refined purification method". Paragraph 0033-0070. . Retrieved 2019/04/02.