4-(5-bromo-1H-indol-3-yl)pyrimidin-2-amine

Base Information

• Chemical Name: 4-(5-bromo-1H-indol-3-yl)pyrimidin-2-amine
• CAS No.: 213473-00-8
• Molecular Formula: C12H9BrN4
• Molecular Weight: 289.13100
• DSSTox Substance ID: DTXSID50434275
• Nikkaji Number: J1.004.111B
• Wikidata: Q82248635
• Pharos Ligand ID: R7GZ8NMRJCB5
• Metabolomics Workbench ID: 134294
• ChEMBL ID: CHEMBL44541
• Mol file: 213473-00-8.mol

Synonyms:2-Pyrimidinamine, 4-(5-bromo-1H-indol-3-yl)-;4-(5-Bromo-1H-indol-3-yl)-2-pyrimidinamine;meridianin C

Chemical Property of 4-(5-bromo-1H-indol-3-yl)pyrimidin-2-amine

Chemical Property:

• Melting Point: 103-106 °C
• Boiling Point: 594.4±60.0 °C(Predicted)
• PKA: 14.31±0.30(Predicted)
• PSA: 68.32000
• Density: 1.680±0.06 g/cm3(Predicted)
• LogP: 2.89970
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 288.00106
• Heavy Atom Count: 17
• Complexity: 275

Purity/Quality:

97% ^*data from raw suppliers

4-(5-Bromo-1H-indol-3-yl)pyrimidin-2-amine 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=CN2)C3=NC(=NC=C3)N

Technology Process of 4-(5-bromo-1H-indol-3-yl)pyrimidin-2-amine

There total 15 articles about 4-(5-bromo-1H-indol-3-yl)pyrimidin-2-amine 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: 95.0%

2-methoxy-ethanol (109-86-4,95507-80-5) + (E)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one (341998-57-0) → Meridianin C (213473-00-8)

Guidance literature:

With guanidine hydrochloride; potassium carbonate; for 4h; Reflux; Inert atmosphere;

DOI:10.1016/j.cplett.2019.01.031

Reference yield: 88.0%

C26H35BrN4O6SSi (1538583-15-1) → Meridianin C (213473-00-8)

Guidance literature:

C₂₆H₃₅BrN₄O₆SSi; With hydrogenchloride; In methanol; water; Reflux;

With sodium hydroxide; In methanol; water; for 4h; pH=14; Reflux;

DOI:10.1021/ol403390m

Reference yield: 73.0%

5-bromo-3-(3-trimethylsilanyl-propynoyl)-indole-1-carboxylic acid tert-butyl ester + guanidine nitrate (113-00-8) → Meridianin C (213473-00-8)

Guidance literature:

With sodium carbonate; In water; acetonitrile; tert-butyl alcohol; at 80 ℃; for 38h;

DOI:10.1002/anie.200501703

upstream raw materials:

guanidine hydrochloride

(E)-1-(5-bromo-1-tosyl-1H-indol-3-yl)-3-(dimethylamino)prop-2-en-1-one

guanidine nitrate

5-bromo-1H-indole