2-[4-[(2E)-2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]pyrazolo[3,4-d]pyrimidin-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Base Information

• Chemical Name: 2-[4-[(2E)-2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]pyrazolo[3,4-d]pyrimidin-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS No.: 78586-43-3
• Molecular Formula: C21H25Cl2N7O4
• Molecular Weight: 510.3737
• NSC Number: 271934
• DSSTox Substance ID: DTXSID90429685
• Mol file: 78586-43-3.mol

Synonyms:NSC271934;78586-43-3;DTXSID90429685;NSC-271934

Chemical Property of 2-[4-[(2E)-2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]pyrazolo[3,4-d]pyrimidin-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol

Chemical Property:

• Vapor Pressure: 1.25E-25mmHg at 25°C
• Boiling Point: 780.2°Cat760mmHg
• Flash Point: 425.6°C
• Density: 1.6g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 509.1345077
• Heavy Atom Count: 34
• Complexity: 655

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=NNC2=C3C=NN(C3=NC=N2)C4C(C(C(O4)CO)O)O)N(CCCl)CCCl
• Isomeric SMILES: C1=CC(=CC=C1/C=N/NC2=C3C=NN(C3=NC=N2)C4C(C(C(O4)CO)O)O)N(CCCl)CCCl

Technology Process of 2-[4-[(2E)-2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]pyrazolo[3,4-d]pyrimidin-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol

There total 3 articles about 2-[4-[(2E)-2-[[4-[bis(2-chloroethyl)amino]phenyl]methylidene]hydrazinyl]pyrazolo[3,4-d]pyrimidin-1-yl]-5-(hydroxymethyl)oxolane-3,4-diol 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: 78.5%

4-hydrazino-1-(β-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidine (64372-76-5) + 4-(bis(2-chloroethyl)amino)benzaldehyde (1208-03-3) → p-benzaldehyde (1-β-D-ribofuranosylpyrazolo<3,4-d>pyrimidin-4-yl)hydrazone (78586-43-3)

Guidance literature:

With 5A molecular sieve; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jm00142a009

Reference yield:

1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidin-4-one (64372-69-6) → p-benzaldehyde (1-β-D-ribofuranosylpyrazolo<3,4-d>pyrimidin-4-yl)hydrazone (78586-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / thionyl chloride, DMF / CH₂Cl₂ / 14 h / 60 °C

2: 70.8 percent / hydrazine / ethanol / 3 h / Heating

3: 78.5 percent / molecular sieves 5A / dimethylformamide / Ambient temperature

With thionyl chloride; 5A molecular sieve; N,N-dimethyl-formamide; hydrazine; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00142a009

Reference yield:

4-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidine (78586-33-1) → p-benzaldehyde (1-β-D-ribofuranosylpyrazolo<3,4-d>pyrimidin-4-yl)hydrazone (78586-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 70.8 percent / hydrazine / ethanol / 3 h / Heating

2: 78.5 percent / molecular sieves 5A / dimethylformamide / Ambient temperature

With 5A molecular sieve; hydrazine; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00142a009

upstream raw materials:

4-hydrazino-1-(β-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidine

4-(bis(2-chloroethyl)amino)benzaldehyde

1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidin-4-one

4-chloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrazolo<3,4-d>pyrimidine