2-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile

Base Information

• Chemical Name: 2-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile
• CAS No.: 865758-95-8
• Molecular Formula: C12H8ClN3O2
• Molecular Weight: 261.667
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID50463469
• Wikidata: Q72449698
• Mol file: 865758-95-8.mol

Synonyms:865758-95-8;2-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile;2-((6-Chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile;2-[(6-chloro-2,4-dioxopyrimidin-1-yl)methyl]benzonitrile;2-[(6-CHLORO-2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)METHYL]BENZONITRILE;2-((6-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl) benzonitrile;JASGBRKRMPRRTD-UHFFFAOYSA-N;SCHEMBL390246;DTXSID50463469;BCP11395;CS-M2294;AKOS015999475;AB54682;Benzonitrile, 2-[(6-chloro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)methyl]-;AC-26400;CS-14697;AM20090702;FT-0769740;C12670;A863130;2-(6-Chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl)-benzonitrile;2-[(6-Chloro-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl)methyl]benzonitrile;Benzonitrile,2-[(6-chloro-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)methyl]-

Chemical Property of 2-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile

Chemical Property:

• PKA: 8.11±0.40(Predicted)
• PSA: 78.91000
• Density: 1.48 g/cm³
• LogP: 1.52228
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 261.0305042
• Heavy Atom Count: 18
• Complexity: 452

Purity/Quality:

99% ^*data from raw suppliers

2-((6-Chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CN2C(=CC(=O)NC2=O)Cl)C#N
• Uses: Alogliptin (A575425) intermediate. 2-((6-Chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile is used as a reactant/ intermediate in discovery of Alogliptin (A575425), which is an antidiabetic agent.

Technology Process of 2-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile

There total 2 articles about 2-((6-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile 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: 93.5%

6-chlorouracil (4270-27-3) + 2-(bromomethyl)benzonitrile (22115-41-9) → 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile (865758-95-8)

Guidance literature:

With sodium hydride; lithium bromide; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 20 ℃; for 12h;

Reference yield: 54.0%

2-(bromomethyl)benzonitrile (22115-41-9) → 2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile (865758-95-8)

Guidance literature:

6-chlorouracil; With sodium hydride; In DMF (N,N-dimethyl-formamide); dimethyl sulfoxide; at 0 ℃; for 0.5h;

With lithium bromide; In DMF (N,N-dimethyl-formamide); dimethyl sulfoxide; at 0 ℃; for 0.25h;

2-(bromomethyl)benzonitrile; In DMF (N,N-dimethyl-formamide); dimethyl sulfoxide; at 0 - 20 ℃;

Reference yield: 84.78%

2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile (865758-95-8) + dimethyl sulfate (77-78-1) → 2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile (865758-96-9)

Guidance literature:

2-[(6-chloro-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]benzonitrile; With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 0.25h;

dimethyl sulfate; In N,N-dimethyl-formamide; for 12h; Solvent; Reagent/catalyst;

upstream raw materials:

6-chlorouracil

2-(bromomethyl)benzonitrile

Downstream raw materials:

2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl)benzonitrile

alogliptin

C₁₄H₁₂ClN₃O₂

alogliptin benzoate

Refernces

• 1、 Deng, Xiaoyan,Jiang, Neng,Jiang, Weizhe,Li, Qing,Meng, Liuwei,Xing, Junhao,Xu, Yanjun. "Identification and structure–activity relationship exploration of uracil-based benzoic acid and ester derivatives as novel dipeptidyl Peptidase-4 inhibitors for the treatment of type 2 diabetes mellitus". . . Retrieved 2021/08/17.
• 2、 -. "PROCESS FOR PREPARATION OF ALOGLIPTIN". Paragraph 0129. . Retrieved 2016/12/12.