N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine

Base Information

• Chemical Name: N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine
• CAS No.: 171179-06-9
• Molecular Formula: C14H12BrN5
• Molecular Weight: 330.187
• Hs Code.: 2933990090
• European Community (EC) Number: 683-576-1
• DSSTox Substance ID: DTXSID20274443
• Nikkaji Number: J746.179H
• Wikidata: Q27088268
• Pharos Ligand ID: WGCV2C9DLHTZ
• ChEMBL ID: CHEMBL53753
• Mol file: 171179-06-9.mol

Synonyms:6-(methylamino)pyrido(3,4-d)pyrimidine;PD 158780;PD-158780;PD158780

Chemical Property of N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine

Chemical Property:

• Vapor Pressure: 4.1E-10mmHg at 25°C
• Melting Point: 174.0 to 178.0 °C
• Refractive Index: 1.768
• Boiling Point: 499.559 °C at 760 mmHg
• PKA: 5.80±0.30(Predicted)
• Flash Point: 255.924 °C
• PSA: 62.73000
• Density: 1.611 g/cm³
• LogP: 3.71860
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 329.02761
• Heavy Atom Count: 20
• Complexity: 316

Purity/Quality:

98%Min ^*data from raw suppliers

PD 158780 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNC1=NC=C2C(=C1)C(=NC=N2)NC3=CC(=CC=C3)Br
• Uses: PD 158780 is a potent tyrosine kinase inhibitor of the epidermal growth factor receptor and has been shown to delay substantial growth of tumors in vivo tumor models.

Technology Process of N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine

There total 7 articles about N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine 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: 91.0%

methylamine (74-89-5) + 4-[(3-bromophenyl)-amino]-6-fluoropyrido[3,4-d]pyrimidine (171179-03-6) → PD158780 (171179-06-9)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃; for 24h;

DOI:10.1021/jm970641d

Reference yield: 34.0%

4-[(3-bromophenyl)-amino]-6-fluoropyrido[3,4-d]pyrimidine (171179-03-6) → PD158780 (171179-06-9)

Guidance literature:

With methylamine; In ethanol;

Reference yield:

6-fluoro-4-oxo-3H-pyrido[3,4-d]pyrimidine (171178-44-2) → PD158780 (171179-06-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / SOCl₂, DMF / 1,2-dichloro-ethane / 2.5 h / Heating

2: 94 percent / propan-2-ol / 0.75 h / Heating

3: 91 percent / dimethylsulfoxide / 24 h / 80 °C

With thionyl chloride; N,N-dimethyl-formamide; In dimethyl sulfoxide; 1,2-dichloro-ethane; isopropyl alcohol;

DOI:10.1021/jm970641d

upstream raw materials:

methylamine

4-[(3-bromophenyl)-amino]-6-fluoropyrido[3,4-d]pyrimidine

m-Bromoaniline

6-fluoro-4-oxo-3H-pyrido[3,4-d]pyrimidine

Refernces

• 1、 Rewcastle, Gordon W.,Murray, Donna K.,Elliott, William L.,Fry, David W.,Howard, Curtis T.,Nelson, James M.,Roberts, Billy J.,Vincent, Patrick W.,Hollis Showalter,Thomas Winters,Denny, William A.. "Tyrosine kinase inhibitors. 14. Structure-activity relationships for methyl-amino-substituted derivatives of 4-[3-bromophenyl)amino]-6- (methylamino)-pyrido[3,4-d]pyrimidine (PD 158780), a potent and specific inhibitor of the tyrosine kinase activity of receptors for the EGF family of growth factors". . p. 742 - 751. Retrieved 2007/10/03.
• 2、 Rewcastle, Gordon W.,Palmer, Brian D.,Thompson, Andrew M.,Bridges, Alexander J.,Cody, Donna R.,Zhou, Hairong,Fry, David W.,McMichael, Amy,Denny, William A.. "Tyrosine kinase inhibitors. 10. Isomeric 4-[(3-bromophenyl)amino]pyrido[d]-pyrimidines are potent ATP binding site inhibitors of the tyrosine kinase function of the epidermal growth factor receptor". . p. 1823 - 1835. Retrieved 2007/10/03.