2(1H)-Pyrimidinone, 4-amino-1-(5-chloro-5-deoxy-beta-D-arabinofuranosyl)-

Base Information

• Chemical Name: 2(1H)-Pyrimidinone, 4-amino-1-(5-chloro-5-deoxy-beta-D-arabinofuranosyl)-
• CAS No.: 32659-31-7
• Molecular Formula: C₉H₁₂ClN₃O₄
• Molecular Weight: 261.665
• NSC Number: 318799
• DSSTox Substance ID: DTXSID10954363
• ChEMBL ID: CHEMBL2357771
• Mol file: 32659-31-7.mol

Synonyms:5'-chloro-5'-deoxyarabinosylcytosine;5'-chloro-araC

Chemical Property of 2(1H)-Pyrimidinone, 4-amino-1-(5-chloro-5-deoxy-beta-D-arabinofuranosyl)-

Chemical Property:

• Vapor Pressure: 4.61E-13mmHg at 25°C
• Boiling Point: 521.7°Cat760mmHg
• PKA: 13.37±0.70(Predicted)
• Flash Point: 269.3°C
• PSA: 110.60000
• Density: 1.86g/cm³
• LogP: -0.73530
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 261.0516336
• Heavy Atom Count: 17
• Complexity: 386

Purity/Quality:

97% ^*data from raw suppliers

DeoxyChlorocytarabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CCl)O)O
• Uses: Deoxy Chlorocytarabine is a lipophilic DNA synthesis inhibitor and has antileukemic activity.

Technology Process of 2(1H)-Pyrimidinone, 4-amino-1-(5-chloro-5-deoxy-beta-D-arabinofuranosyl)-

There total 4 articles about 2(1H)-Pyrimidinone, 4-amino-1-(5-chloro-5-deoxy-beta-D-arabinofuranosyl)- 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: 83.5%

<2R-(2α,3β,3aβ,9aβ)>-2-chloromethyl-2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-6H-furo<2',3':4,5>oxazolo<3,2-a>pyrimidine hydrochloride (32659-29-3) → 4-Amino-1-(5-chloro-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2-(1H)-one (32659-31-7)

Guidance literature:

With Dowex 1X₄(CO₃^(2-)); In water; for 1h; Ambient temperature;

Reference yield:

5'-chloro-5'-deoxy-2',3'-O-sulphinylcytidine hydrochloride (69260-61-3) → 4-Amino-1-(5-chloro-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2-(1H)-one (32659-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / dimethylformamide / 0.75 h / 100 °C

2: 83.5 percent / Dowex 1X₄(CO₃^(2-)) / H₂O / 1 h / Ambient temperature

With Dowex 1X₄(CO₃^(2-)); In water; N,N-dimethyl-formamide;

Reference yield:

5'-chloro-5'-deoxycytidine (31652-78-5) → 4-Amino-1-(5-chloro-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2-(1H)-one (32659-31-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / SOCl₂ / acetonitrile / 3 h

2: 78 percent / dimethylformamide / 0.75 h / 100 °C

3: 83.5 percent / Dowex 1X₄(CO₃^(2-)) / H₂O / 1 h / Ambient temperature

With thionyl chloride; Dowex 1X₄(CO₃^(2-)); In water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

<2R-(2α,3β,3aβ,9aβ)>-2-chloromethyl-2,3,3a,9a-tetrahydro-3-hydroxy-6-imino-6H-furo<2',3':4,5>oxazolo<3,2-a>pyrimidine hydrochloride

5'-chloro-5'-deoxy-2',3'-O-sulphinylcytidine hydrochloride

5'-chloro-5'-deoxycytidine

Downstream raw materials:

4-Amino-1-(2,5-anhydro-β-D-arabinofuranosyl)pyrimidin-2(1H)-one

Refernces

• 1、 Hrebabecky, Hubert,Brokes, Josef,Beranek, Jiri. "REACTION OF NUCLEOSIDES WITH THIONYL CHLORIDE; PREPARATION OF THE DEOXY DERIVATIVES OF CYTIDINE AND ADENOSINE". . p. 599 - 605. Retrieved 2007/10/02.