(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine

Base Information

• Chemical Name: (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine
• CAS No.: 330784-23-1
• Molecular Formula: C₁₉H₂₃ClN₄O₃
• Molecular Weight: 390.87
• Mol file: 330784-23-1.mol

Synonyms:(S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine

Chemical Property of (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine

There total 6 articles about (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine 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: 60.0%

4-(3-Chloro-4-methoxy-benzylamino)-2-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-pyrimidine-5-carbaldehyde (330785-87-0) + methyllithium (917-54-4) → (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine (330784-23-1)

Guidance literature:

4-(3-Chloro-4-methoxy-benzylamino)-2-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-pyrimidine-5-carbaldehyde; methyllithium; In tetrahydrofuran; diethyl ether; at -78 ℃;

With manganese(IV) oxide; In tetrahydrofuran; diethyl ether; chloroform; at 20 ℃;

DOI:10.1016/j.bmcl.2015.02.041

Reference yield:

ethyl 4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylate (330785-81-4) → (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine (330784-23-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C

2.1: manganese(IV) oxide / dichloromethane / 20 °C

3.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0 °C

3.2: 0 °C

4.1: tetrahydrofuran; diethyl ether / -78 °C

4.2: 20 °C

With manganese(IV) oxide; lithium aluminium tetrahydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform;

DOI:10.1016/j.bmcl.2015.02.041

Reference yield:

4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylic acid (330786-34-0) → (S)-2-(2-hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-acetylpyrimidine (330784-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: manganese(IV) oxide / dichloromethane / 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 0 °C

2.2: 0 °C

3.1: tetrahydrofuran; diethyl ether / -78 °C

3.2: 20 °C

With manganese(IV) oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform;

DOI:10.1016/j.bmcl.2015.02.041

upstream raw materials:

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

4-[(3-chloro-4-methoxybenzyl)amino]-2-(methylsulfanyl)pyrimidine-5-carboxylic acid

4-(3-Chloro-4-methoxy-benzylamino)-2-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-pyrimidine-5-carbaldehyde

methyllithium