N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide

Base Information

• Chemical Name: N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide
• CAS No.: 1150103-18-6
• Molecular Formula: C₁₃H₁₅N₃O₄S
• Molecular Weight: 309.346
• Mol file: 1150103-18-6.mol

Synonyms:N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide

Chemical Property of N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide

There total 3 articles about N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide 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: 42.0%

ethyl 4-methyl-2-({4-[(methylsulfonyl)amino]phenyl}oxy)-5-pyrimidinecarboxylate (1150103-17-5) → N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide (1150103-18-6)

Guidance literature:

ethyl 4-methyl-2-({4-[(methylsulfonyl)amino]phenyl}oxy)-5-pyrimidinecarboxylate; With diisobutylaluminium hydride; In dichloromethane; at -78 - 0 ℃; for 1.5h;

With water; rochelle salt; In dichloromethane; for 1h;

Reference yield:

4-(methylsulfonylamino)phenol (51767-39-6) → N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide (1150103-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 80 °C

2: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C

With diisobutylaluminium hydride; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.08.080

Reference yield:

2-chloro-4-methylpyrimidine-5-carboxylic acid ethyl ester (188781-08-0) → N-(4-{[5-(hydroxymethyl)-4-methyl-2-pyrimidinyl]oxy}phenyl)methanesulfonamide (1150103-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 80 °C

2: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C

With diisobutylaluminium hydride; caesium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.08.080

upstream raw materials:

ethyl 4-methyl-2-({4-[(methylsulfonyl)amino]phenyl}oxy)-5-pyrimidinecarboxylate

4-(methylsulfonylamino)phenol

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

Downstream raw materials:

N-{4-[(5-formyl-4-methyl-2-pyrimidinyl)oxy]phenyl}methanesulfonamide

5-({[(3-fluorophenyl)(1-{[4-methyl-2-({4-[(methylsulfonyl)amino]phenyl}oxy)-5-pyrimidinyl]methyl}-4-piperidinyl)amino]carbonyl}amino)-2-pyridinecarboxamide