Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate

Base Information

• Chemical Name: Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate
• CAS No.: 2134-36-3
• Molecular Formula: C8H9ClN2O2
• Molecular Weight: 200.625
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID70506549
• Wikidata: Q72473699
• Mol file: 2134-36-3.mol

Synonyms:ethyl 4-chloro-2-methylpyrimidine-5-carboxylate;2134-36-3;MFCD08275064;ethyl4-chloro-2-methylpyrimidine-5-carboxylate;SCHEMBL427402;DTXSID70506549;LXIAVLIGRIDNHQ-UHFFFAOYSA-N;CAA13436;AKOS005146390;CS-W022687;GS-5799;PB31058;SY098645;AM20090187;FT-0721459;A15371;EN300-107576;ethyl-2-methyl-4-chloropyrimidine-5-carboxylate;Z1269141696

Chemical Property of Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate

Chemical Property:

• Vapor Pressure: 0.00487mmHg at 25°C
• Melting Point: 31 °C
• Refractive Index: 1.524
• Boiling Point: 276.187 °C at 760 mmHg
• PKA: -1.16±0.29(Predicted)
• Flash Point: 120.834 °C
• PSA: 52.08000
• Density: 1.266 g/cm³
• LogP: 1.61510
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 200.0352552
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl4-chloro-2-methylpyrimidine-5-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C(N=C1Cl)C

Technology Process of Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate

There total 4 articles about Ethyl 4-chloro-2-methylpyrimidine-5-carboxylate 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: 57.7%

ethyl 3,4-dihydro-4-oxo-2-methylpyrimidine-5-carboxylate (53135-24-3) → ethyl 4-chloro-2-methylpyrimidine-5-carboxylate (2134-36-3)

Guidance literature:

With trichlorophosphate; for 0.5h; Reflux;

Reference yield:

ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate (53135-24-3) → ethyl 4-chloro-2-methylpyrimidine-5-carboxylate (2134-36-3)

Guidance literature:

With trichlorophosphate;

DOI:10.1016/S0960-894X(00)00312-7

Reference yield:

diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 4-chloro-2-methylpyrimidine-5-carboxylate (2134-36-3)

Guidance literature:

Multi-step reaction with 2 steps

1: EtONa / ethanol

2: POCl₃

With sodium ethanolate; trichlorophosphate; In ethanol; 1: Cyclization / 2: Chlorination;

DOI:10.1016/S0960-894X(00)00312-7

upstream raw materials:

ethyl 3,4-dihydro-4-oxo-2-methylpyrimidine-5-carboxylate

ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

4-{Butyl-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-2-methyl-pyrimidine-5-carboxylic acid

4-{Butyl-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-2-methyl-pyrimidine-5-carboxylic acid ethyl ester

2-Methyl-4-{[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-pyrimidine-5-carboxylic acid ethyl ester

4-{Ethyl-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-2-methyl-pyrimidine-5-carboxylic acid ethyl ester

Refernces

• 1、 Scott, James S.,Gill, Adrian L.,Godfrey, Linda,Groombridge, Sam D.,Rees, Amanda,Revill, John,Schofield, Paul,S?rme, Pernilla,Stocker, Andrew,Swales, John G.,Whittamore, Paul R.O.. "Optimisation of pharmacokinetic properties in a neutral series of 11β-HSD1 inhibitors". . p. 6756 - 6761. Retrieved 2013/01/14.
• 2、 Palanki, Moorthy S.S.,Erdman, Paul E.,Manning, Anthony M.,Ow, Arnold,Ransone, Lynn J.,Spooner, Cheryl,Suto, Carla,Suto, Mark. "Novel inhibitors of AP-1 and NF-κB mediated gene expression: Structure-activity relationship studies of ethyl 4-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-2-(trifluoromethyl)pyrimidine-5-carb oxylate". . p. 1645 - 1648. Retrieved 2007/10/03.