5H-Cyclopentapyrimidine, 6,7-dihydro- (6CI,7CI,8CI,9CI)

Base Information

• Chemical Name: 5H-Cyclopentapyrimidine, 6,7-dihydro- (6CI,7CI,8CI,9CI)
• CAS No.: 5661-00-7
• Molecular Formula: C₇H₈N₂
• Molecular Weight: 120.154
• Mol file: 5661-00-7.mol

Synonyms:4,5-Trimethylenepyrimidine;6,7-Dihydro-5H-cyclopenta[d]pyrimidine

Chemical Property of 5H-Cyclopentapyrimidine, 6,7-dihydro- (6CI,7CI,8CI,9CI)

Chemical Property:

• Boiling Point: 224℃
• Flash Point: 95℃
• PSA: 25.78000
• Density: 1.144
• LogP: 0.96530

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 5H-Cyclopentapyrimidine, 6,7-dihydro- (also known as 4,5-trimethylenepyrimidine or 6,7-dihydro-5H-cyclopenta[d]pyrimidine) is a key scaffold in the design of novel vascular endothelial growth factor receptor 2 (VEGFR 2) inhibitors, demonstrating promising anti-cancer potential. Derivatives of this scaffold, such as compounds 6c and 6b, exhibit significant VEGFR 2 inhibition, with 97% and 87% enzyme inhibition at 10 μM, respectively. By targeting VEGFR 2, these compounds disrupt angiogenesis, thereby suppressing tumor growth and metastasis, highlighting their therapeutic relevance in cancer treatment.

Technology Process of 5H-Cyclopentapyrimidine, 6,7-dihydro- (6CI,7CI,8CI,9CI)

There total 13 articles about 5H-Cyclopentapyrimidine, 6,7-dihydro- (6CI,7CI,8CI,9CI) 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: 85.0%

cyclopentanone (120-92-3) + 3-methyl-5-nitro-4(3H)-pyrimidinone (17758-33-7) → 5H-6,7-dihydrocyclopentapyrimidine (5661-00-7)

Guidance literature:

With ammonium acetate; In methanol; at 65 ℃; for 48h;

Reference yield: 85.0%

1,3,5-Triazine (290-87-9) + cyclopentanone (120-92-3) → 5H-6,7-dihydrocyclopentapyrimidine (5661-00-7)

Guidance literature:

With triethylamine; pyrrolidine-2-carboxylic acid amide; In dimethyl sulfoxide; at 90 ℃; for 24h; regioselective reaction;

DOI:10.1039/c5ra16995j

Reference yield: 72.0%

1,3,5-Triazine (290-87-9) + 1-pyrrolidinocyclopent-1-ene (7148-07-4) → 5H-6,7-dihydrocyclopentapyrimidine (5661-00-7)

Guidance literature:

In 1,4-dioxane; at 90 ℃; for 5h;

DOI:10.1021/jo00134a034

upstream raw materials:

4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

2-chlorocyclopent-1-ene-1-carbaldehyde

formamide

cyclopentanone

Downstream raw materials:

2-amino-3-cyano-5,6-trimethylenepyridine

Refernces

3D-QSAR pharmacophore modelling, virtual screening and docking studies for lead discovery of a novel scaffold for VEGFR 2 inhibitors: Design, synthesis and biological evaluation

10.1016/j.bioorg.2019.102988

The study focuses on the design, synthesis, and biological evaluation of a novel chemical scaffold, 6,7-dihydro-5H-cyclopenta[d]pyrimidine derivatives, as inhibitors of vascular endothelial growth factor receptor 2 (VEGFR 2). The research involved molecular modeling protocols, including 3D-QSAR pharmacophore modeling, virtual screening, and docking studies, to identify and design potential VEGFR 2 inhibitors. The chemicals used in the study include a series of synthesized 6,7-dihydro-5H-cyclopenta[d]pyrimidine derivatives, with compounds 6c and 6b showing significant enzyme inhibition of 97% and 87% at 10 μM, respectively. These compounds were designed to target the VEGFR 2 receptor, which plays a crucial role in angiogenesis and is a key therapeutic target for inhibiting tumor growth and metastasis. The purpose of these chemicals was to serve as potential anti-cancer agents by inhibiting the VEGFR 2 signaling pathway, thereby affecting the blood supply to tumor cells and inhibiting their growth and spread.