330785-81-4

Basic information

• Product Name: (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)
• Synonyms: (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester);4-(3-Chloro-4-Methoxy-benzylaMino)-2-Methylsulfanyl-pyriMidine-5-carboxylic acid ethyl ester;4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-(methylthio)-5-pyrimidinecarboxylic acid ethyl ester;4-(3-chloro-4-MethoxybenzylaMino)-5-ethoxycarbonyl-2-MethylthiopyriMidine;ethyl 4-(3-chloro-4-MethoxybenzylaMino)-2-(Methylthio)pyriMidine-5-carboxylate;Ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulphanyl)pyrimidine-5-carboxylate, 4-[(3-Chloro-4-methoxybenzyl)amino]-5-(ethoxycarbonyl)-2-(methylthio)pyrimidine;Avanafil Intermediate II;(5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)###NA
• CAS NO: 330785-81-4
• Molecular Formula: C₁₆H₁₈ClN₃O₃S
• Molecular Weight: 367.85042
• EINECS: -0
• Mol File: 330785-81-4.mol

Chemical Properties

• Boiling Point: 514.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.33±0.1 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 2.70±0.10(Predicted)
• CAS DataBase Reference: (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)(CAS DataBase Reference)
• NIST Chemistry Reference: (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)(330785-81-4)
• EPA Substance Registry System: (5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester)(330785-81-4)

Safety Data

• Hazardous Substances Data: 330785-81-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(5-PyriMidinecarboxylic acid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester) is used as a key intermediate in the synthesis of Avanafil, a PDE5 inhibitor, for the treatment of erectile dysfunction. Its role in the production of Avanafil is essential, as it contributes to the development of a medication that helps improve the quality of life for patients suffering from this condition.
Used in Research and Development:
(5-PyriMidinecarboxylicacid, 4-[[(3-chloro-4-Methoxyphenyl)Methyl]aMino]-2-(Methylthio)-,ethyl ester) is also utilized in research and development for the discovery and development of new PDE5 inhibitors and other related pharmaceuticals. Its unique chemical structure makes it a valuable tool for understanding the interactions between PDE5 enzymes and potential therapeutic agents, ultimately leading to the creation of more effective treatments for various conditions.

Upstream product

• 5909-24-0 4-chloro-2-methanesulfanylpyrimidine-5-carboxylic acid ethyl ester 
• 115514-77-7 (3-chloro-4-methoxyphenyl)methanamine 
• 41965-95-1 (3-chloro-4-methoxyphenyl)methylamine hydrogen chloride 
• 53554-29-3 ethyl 4-hydroxy-2-(methylthio)pyrimidine-5-carboxylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 330785-82-5 4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylsulfinylpyrimidine 

Downstream Products

• 330785-82-5 4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-methylsulfinylpyrimidine 
• 330785-85-8 [4-(3-Chloro-4-methoxy-benzylamino)-2-methylsulfanyl-pyrimidin-5-yl]-methanol 
• 330786-34-0 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylic acid 
• 372117-76-5 2-methylsulfonyl-5-ethoxycarbonyl-4-(3-chloro-4-methoxybenzylamino)pyrimidine 
• 372113-63-8 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyridylmethyl)carbamoyl]pyrimidine 
• 330784-22-0 (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(pyridin-2-ylmethyl)carbamoyl]pyrimidine 
• 330784-47-9 avanafil 
• 330786-00-0 2-chloro-4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonylpyrimidine 

Relevant articles and documents

A kind of avanafil impurity D and synthesis method and application thereof

The present invention provides a new aphranarfil impurity and synthesis method thereof, by synthesizing and characterizing the impurity, the structure of the impurity is determined, the drug impurity profile of avanafil is perfected, the resulting product is of high purity, can be used as a control for drug quality control research.

Preparation method of avanafil

The invention provides a preparation method of avanafil, and specifically relates to the technical field of pharmaceutical chemistry. The preparation method of avanafil comprises the following steps:sequentially carrying out cyclization and chlorination reactions on methyl thiourea sulfuric acid and diethyl ethoxymethylene malonate which serve as initial raw materials to obtain 4-chloro-2-methylthiopyrimidine-5-carboxylic acid ethyl ester; then substituting and hydrolyzing with 3-chloro-4-methoxybenzylamine; condensing with 2-pyrimidinemethanamine to obtain a key intermediate, namely, 4-[(3-chloro-methoxybenzyl)amino]-2-methylthio-N-(2-pyrimidine methyl)-5-pyrimidine formamide; oxidizing the intermediate and reacting with L-prolinol to generate the avanafil. The preparation method has theadvantages of easy availability of raw materials, easiness and convenience in operation, mild reaction conditions and higher product yield.

A process for the preparation of atorvastatin that non-intermediate and its preparation method

The invention provides a novel intermediate IV which is used for preparation of avanafil. The intermediate has a general formula IV as described in the specification; and in the general formula IV, R represents a C1-20 alkylsulfinyl group or a C1-20 alkylsulfonyl group. The intermediate has high purity, is suitable for industrial production and can be subjected to a one-step chemical reaction to prepare avanafil. The invention also provides a preparation method for the intermediate and a method for preparing avanafil from the intermediate.

Atorvastatin that non-synthetic method

The invention provides a synthesis method of avanafil. The synthesis method of avanafil comprises the following steps: carrying out nucleophilic substitution reaction with a compound (13) or a compound (3) by a compound (18), hydrolyzing to prepare a compound (21) or a compound (22), reacting the compound (21) or the compound (22) with sulfonic acid chloride or pivaloyl chloride to obtain mixed anhydride, reacting the mixed anhydride with a compound (23) to prepare a compound (24) or a compound (25), then oxidizing the compound (24), subsequently reacting the compound (24) with a compound (9) to prepare avanafil, or directly reacting the compound (25) with the compound (9) to prepare avanafil. The synthesis method is high in controllability, simple in step, high in yield and low in cost, and is suitable for industrial production. The reaction route is shown in the description.

Prodrugs Of Bicyclic Substituted Pyrimidine Type PDE-5 Inhibitors

Provided are prodrugs of a bicyclic substituted pyrimidine type PDE-5 inhibitors, pharmaceutically acceptable salts or stereoisomers thereof. Also provided are methods for preparing these prodrug compounds, pharmaceutical preparations, and pharmaceutical compositions, as well as a use of these compounds, pharmaceutical preparations and pharmaceutical compositions in the manufacture of medicaments for treatment and/or prophylaxis of sexual dysfunction and lower urinary tract symptoms.

8-(3-Chloro-4-methoxybenzyl)-8H-pyrido[2,3-d]pyrimidin-7-one derivatives as potent and selective phosphodiesterase 5 inhibitors

A novel series of highly selective phosphodiesterase 5 (PDE5) inhibitors was found. 8H-Pyrido[2,3-d]pyrimidin-7-one derivatives bearing an (S)-2-(hydroxymethyl)pyrrolidin-1-yl group at the 2-position and a 3-chloro-4-methoxybenzyl group at the 8-position

BICYCLIC SUBSTITUTED PYRIMIDINE COMPOUNDS

The present invention relates to the technical field of medicine and pharmacy, and particularly relates to bicyclic group substituted pyrimidine compounds represented by general formula (I), pharmaceutical acceptable salts thereof or stereoisomers thereof, wherein R1, R2, R3, R4, R5 and R6 are as defined in the specification. The present invention also relates to preparation methods, pharmaceutical formulations, and pharmaceutical compositions of the compounds, and use of the compounds, pharmaceutical formulations, and pharmaceutical compositions for preparing a medicament for treating and/or preventing sexual dysfuntion diseases and diseases with lower urinay tract symptoms.

A PROCESS FOR THE PREPARATION OF AVANAFIL AND ITS NOVEL INTERMEDIATES

The present invention relates to a novel compound of Formula (II), and its use in preparation of Avanafil, [Formula should be inserted here] wherein R is -OH, -CI or -OR1 and R1 is C1 to C3 alkyl group.

PROCESS FOR THE PREPARATION OF (S)-4-[(3-CHLORO-4-METHOXYBENZYL)AMINO]-2-[2- (HYDROXYMETHYL)-1-PYRROLIDINYL]-N-(2-PYRIMIDINYL METHYL-5-PYRIMIDINE CARBOXAMIDE

The present invention relates to an improved process for the preparation of (S)-4-[(3- chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinyl ethyl)- 5-pyrimidine carboxamide compound of formula-1 represented by the following structural formula.

The discovery of avanafil for the treatment of erectile dysfunction: A novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor

Novel pyrimidine-5-carboxamide derivatives bearing a 3-chloro-4-methoxybenzylamino group at the 4-position were identified as potent and highly selective phosphodiesterase 5 inhibitors. Among them, we successfully found 10j (avanafil) which exhibited a potent relaxant effect on isolated rabbit cavernosum (EC30 = 2.1 nM) and a high isozyme selectivity.