2,8-Dichloropyrimido[5,4-D]pyrimidine

Base Information

• Chemical Name: 2,8-Dichloropyrimido[5,4-D]pyrimidine
• CAS No.: 189747-34-0
• Molecular Formula: C6H2Cl2N4
• Molecular Weight: 199.97
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80443996
• Wikidata: Q82261998
• Mol file: 189747-34-0.mol

Synonyms:2,8-DICHLOROPYRIMIDO[5,4-D]PYRIMIDINE;189747-34-0;4,6-dichloropyrimido[5,4-d]pyrimidine;Pyrimido[5,4-d]pyrimidine, 2,8-dichloro-;2,8-DICHLOROPYRIMIDO[5,4-D][1,3]DIAZINE;SCHEMBL23537882;DTXSID80443996;MFCD09702010;AKOS015907647;AB51062;BS-42771;CS-0183173;FT-0645576;4,6-bis(chloranyl)pyrimido[5,4-d]pyrimidine;A813351;2,8-Dichloropyrimido[5,4-d]pyrimidine, AldrichCPR;J-507544

Chemical Property of 2,8-Dichloropyrimido[5,4-D]pyrimidine

Chemical Property:

• Refractive Index: 1.695
• PSA: 51.56000
• Density: 1.67 g/cm³
• LogP: 1.72660
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 199.9656515
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

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

2,8-Dichloropyrimido[5,4-d]pyrimidine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C2C(=NC(=N1)Cl)C(=NC=N2)Cl

Technology Process of 2,8-Dichloropyrimido[5,4-D]pyrimidine

There total 8 articles about 2,8-Dichloropyrimido[5,4-D]pyrimidine 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:

6-chloropyrimido(5,4-d)pyrimidin-4-ol → 2,8-dichloropyrimido(5,4-d)pyrimidine (189747-34-0)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; at 90 ℃; for 11h;

Reference yield:

ethyl 5-amino-2-chloropyrimidine-4-carboxylate (59950-50-4) → 2,8-dichloropyrimido(5,4-d)pyrimidine (189747-34-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / NH₃(gas) / ethanol / 48 h / 100 °C

2: 81 percent / 6 h / 100 °C

3: SOCl₂, DMF / 0.5 h

With thionyl chloride; ammonia; N,N-dimethyl-formamide; In ethanol;

DOI:10.1021/jm960879m

Reference yield:

5-amino-2-chloropyrimidine-4-carboxamide (189747-29-3) → 2,8-dichloropyrimido(5,4-d)pyrimidine (189747-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / 6 h / 100 °C

2: SOCl₂, DMF / 0.5 h

With thionyl chloride; N,N-dimethyl-formamide;

DOI:10.1021/jm960879m

upstream raw materials:

6-chloropyrimido[5,4-d]pyrimidin-4(3H)-one

ethyl 5-amino-2-chloropyrimidine-4-carboxylate

5-amino-2-chloropyrimidine-4-carboxamide

orotic acid

Refernces

• 1、 Rewcastle, Gordon W.,Bridges, Alexander J.,Fry, David W.,Rubin, J. Ronald,Denny, William A.. "Tyrosine kinase inhibitors. 12. Synthesis and structure-activity relationships for 6-substituted 4-(phenylamino)pyrimido[5,4-d]pyrimidines designed as inhibitors of the epidermal growth factor receptor". . p. 1820 - 1826. Retrieved 2007/10/03.