2-Chloro-4-(pyrrolidin-1-yl)pyrimidine

Base Information

• Chemical Name: 2-Chloro-4-(pyrrolidin-1-yl)pyrimidine
• CAS No.: 35691-20-4
• Molecular Formula: C8H10 Cl N3
• Molecular Weight: 183.64
• Hs Code.: 2933990090
• European Community (EC) Number: 689-884-2
• DSSTox Substance ID: DTXSID00444662
• Nikkaji Number: J461.982J
• Wikidata: Q82262869
• Mol file: 35691-20-4.mol

Synonyms:2-chloro-4-(pyrrolidin-1-yl)pyrimidine;35691-20-4;2-chloro-4-pyrrolidin-1-ylpyrimidine;4-azetidin-1-yl-2-chloropyrimidine;Pyrimidine, 2-chloro-4-(1-pyrrolidinyl)-;2-chloro-4-pyrrolidin-1-yl-pyrimidine;SCHEMBL3949154;2-Chloro-4-pyrrolizinopyrimidine;DTXSID00444662;MFCD09475891;STL102679;AKOS005716894;DS-1924;PS-3467;SB57291;BL008130;CS-0042698;EN300-71600;A822941;2-chloro-4-(pyrrolidin-1-yl)pyrimidine, AldrichCPR;Z976662392

Chemical Property of 2-Chloro-4-(pyrrolidin-1-yl)pyrimidine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.582
• Boiling Point: 348.6°Cat760mmHg
• Flash Point: 164.6°C
• PSA: 29.02000
• Density: 1.289g/cm³
• LogP: 1.79520
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 183.0563250
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

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

2-Chloro-4-(pyrrolidin-1-yl)pyrimidine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)C2=NC(=NC=C2)Cl
• Uses: 4-(Azetidin-1-yl)-2-chloropyrimidine is a reagent in the preparation of pyrimidinyl biphenylureas as allosteric modulators of the cannabinoid receptor 1 (CB1).

Technology Process of 2-Chloro-4-(pyrrolidin-1-yl)pyrimidine

There total 3 articles about 2-Chloro-4-(pyrrolidin-1-yl)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: 87.0%

pyrrolidine (123-75-1) + 2,6-Dichloropyrimidine (3934-20-1) → 2-Chloro-4-(pyrrolidin-1-yl)pyrimidine (35691-20-4)

Guidance literature:

2,6-Dichloropyrimidine; With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; In N,N-dimethyl-formamide; for 0.0833333h; Schlenk technique; Inert atmosphere;

pyrrolidine; With triethylamine; In N,N-dimethyl-formamide; at 23 ℃; for 4h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03854

Reference yield: 77.3%

pyrrolidine (123-75-1) + 2,6-Dichloropyrimidine (3934-20-1) → 2-Chloro-4-(pyrrolidin-1-yl)pyrimidine (35691-20-4) + 4-chloro-2-(pyrrolidin-1-yl)pyrimidine (33852-01-6)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b01448

Reference yield: 70.0%

→ 2-Chloro-4-(pyrrolidin-1-yl)pyrimidine (35691-20-4)

Guidance literature:

In ethanol; at 20 ℃; for 12h;

upstream raw materials:

pyrrolidine

2,6-Dichloropyrimidine

Downstream raw materials:

benzyl 2-(4-(pyrrolidin-1-yl)pyrimidin-2-yl)ethylcarbamate

Refernces

• 1、 Wang, Linxiao,Zhang, Qian,Wang, Zhe,Zhu, Wufu,Tan, Ninghua. "Design, synthesis, docking, molecular dynamics and bioevaluation studies on novel N-methylpicolinamide and thienopyrimidine derivatives with inhibiting NF-κB and TAK1 activities: Cheminformatics tools RDKit applied in drug design". . . Retrieved 2021/07/09.
• 2、 Jo, Jeyun,Kim, Sou Hyun,Kim, Heegyu,Jeong, Myeonggyo,Kwak, Jae-Hwan,Taek Han, Young,Jeong, Jee-Yeong,Jung, Young-Suk,Yun, Hwayoung. "Discovery and SAR studies of novel 2-anilinopyrimidine-based selective inhibitors against triple-negative breast cancer cell line MDA-MB-468". supporting information. p. 62 - 65. Retrieved 2018/11/23.