Ethyl 4-[5-[(2-ethoxypyrimidin-5-yl)methyl]-2-[(4-fluorophenyl)methylsulfanyl]-4-oxopyrimidin-1-yl]benzoate

Base Information

• Chemical Name: Ethyl 4-[5-[(2-ethoxypyrimidin-5-yl)methyl]-2-[(4-fluorophenyl)methylsulfanyl]-4-oxopyrimidin-1-yl]benzoate
• CAS No.: 306974-70-9
• Molecular Formula: C₂₇H₂₅FN₄O₄S
• Molecular Weight: 520.584
• ChEMBL ID: CHEMBL4303679
• DSSTox Substance ID: DTXSID80470686
• Nikkaji Number: J2.931.004A
• Pharos Ligand ID: H5Z49MGKGB5D
• Wikidata: Q27077936
• Mol file: 306974-70-9.mol

Synonyms:GW1100

Chemical Property of Ethyl 4-[5-[(2-ethoxypyrimidin-5-yl)methyl]-2-[(4-fluorophenyl)methylsulfanyl]-4-oxopyrimidin-1-yl]benzoate

Chemical Property:

• Melting Point: 208-210℃
• Boiling Point: 690.2±65.0 °C(Predicted)
• PKA: 1.20±0.22(Predicted)
• PSA: 121.50000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 4.62010
• Storage Temp.: +2C to +8C
• Solubility.: Soluble in DMSO (up to 2 mg/ml) or in DMF (up to 5 mg/ml).
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 520.15805463
• Heavy Atom Count: 37
• Complexity: 832

Purity/Quality:

97% ^*data from raw suppliers

GW 1100 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=NC=C(C=N1)CC2=CN(C(=NC2=O)SCC3=CC=C(C=C3)F)C4=CC=C(C=C4)C(=O)OCC
• Description: GW1100 (306974-70-9) is a selective antagonist of GPR40. GW1100 inhibits GRP40-mediated Ca2+?increases stimulated by GW9508 (Cat.# 10-1108) or linoleic acid (pIC50?= 5.99 for either agonist).1?The effects of GPR40 activation on insulin secretion in cells are also blocked by the addition of GW1100. GW1100 does not influence calcium mobilization mediated by GPR120.
• Uses: GW 1100 is a selective G protein-coupled receptor GPR40 antagonist. GW 1100 has been shown to reverse the effects GPR40 agonists which induce glucose-stimulated insulin secretion.

Technology Process of Ethyl 4-[5-[(2-ethoxypyrimidin-5-yl)methyl]-2-[(4-fluorophenyl)methylsulfanyl]-4-oxopyrimidin-1-yl]benzoate

There total 7 articles about Ethyl 4-[5-[(2-ethoxypyrimidin-5-yl)methyl]-2-[(4-fluorophenyl)methylsulfanyl]-4-oxopyrimidin-1-yl]benzoate 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: 48.0%

C20H20N4O4S (306974-64-1) + 4-Fluorobenzyl bromide (459-46-1) → GW1100 (306974-70-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.3987/COM-11-12175

Reference yield:

ethyl 3-(2-ethoxypyrimidin-5-yl)propionate (1314534-00-3) → GW1100 (306974-70-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 0 - 20 °C

1.2: 4 h / 0 °C

1.3: 20 °C

2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C

3.1: acetonitrile / 20 h / 20 °C

4.1: triethylamine / N,N-dimethyl-formamide / 20 °C

5.1: sulfuric acid / N,N-dimethyl-formamide / 5 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

With oxalyl dichloride; sulfuric acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.3987/COM-11-12175

Reference yield:

2-(methoxymethylene)-3-(2-ethyoxypyrimidin-5-yl)propionic acid → GW1100 (306974-70-9)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C

2: acetonitrile / 20 h / 20 °C

3: triethylamine / N,N-dimethyl-formamide / 20 °C

4: sulfuric acid / N,N-dimethyl-formamide / 5 h / 20 °C

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

With oxalyl dichloride; sulfuric acid; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.3987/COM-11-12175

upstream raw materials:

C₂₀H₂₀N₄O₄S

4-Fluorobenzyl bromide

ethyl 3-(2-ethoxypyrimidin-5-yl)acrylate

ethyl 3-(2-ethoxypyrimidin-5-yl)propionate