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

Base Information

• Chemical Name: 5-PyriMidinecarboxylic acid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)- 1-pyrrolidinyl]-
• CAS No.: 330785-84-7
• Molecular Formula: C18H21ClN4O4
• Molecular Weight: 392.842
• Hs Code.: 2933990090
• Mol file: 330785-84-7.mol

Synonyms:5-PyriMidinecarboxylic acid,4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)-1-pyrrolidinyl];(S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic acid;

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

Chemical Property:

• Melting Point: >176oC (dec.)
• Boiling Point: 647.6±65.0 °C(Predicted)
• PKA: 1.80±0.36(Predicted)
• PSA: 111.04000
• Density: 1.415±0.06 g/cm3 (20 oC 760 Torr)
• LogP: 1.89690
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99%min ^*data from raw suppliers

(S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-4-((3-Chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)pyrimidine-5-carboxylic Acid is used in the preparation of an Avanafil (A794670) intermediate. Avanafil is a phosphodiesterase (PDE5) inhibitor, used to treat erectile dysfunction.

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

There total 20 articles about 5-PyriMidinecarboxylic acid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-[(2S)-2-(hydroxyMethyl)- 1-pyrrolidinyl]- 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: 98.9%

ethyl (S)-4-((3-chloro-4-methoxybenzyl)amino)-2-(2-(hydroxymethyl)tetrahydropyrrole-1-yl)-5-pyrimidinecarboxylate (1638497-22-9,330785-83-6) → 4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid (330785-84-7)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 40 ℃;

Reference yield: 87.0%

tert-butyl 4-(3-chloro-4-methoxybenzylamino)-2-[(S)-2-hydroxymethylpyrrolidinyl-1-yl]-5-pyrimidinecarboxylate → 4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid (330785-84-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

Reference yield:

ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate (53554-29-3) → 4-{[(3-chloro-4-methoxyphenyl)methyl]amino}-2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]pyrimidine-5-carboxylic acid (330785-84-7)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 5 °C

4: triethylamine / dichloromethane / 5 - 10 °C

5: sodium hydroxide / water / 8.17 h / 25 - 100 °C

With sodium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium hydroxide; trichlorophosphate; In dichloromethane; water; toluene;

upstream raw materials:

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

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

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

2-chloro-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine

Downstream raw materials:

avanafil

Refernces

• 1、 -. "Preparation method of avanafil impurity". Paragraph 0031; 0051-0056. . Retrieved 2021/05/19.
• 2、 -. "Method for preparing avanafil raw material medicine". Paragraph 0047; 0069; 0070; 0071. . Retrieved 2017/08/28.