6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione

Base Information

• Chemical Name: 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione
• CAS No.: 5466-00-2
• Molecular Formula: C7H8N2O2
• Molecular Weight: 152.153
• Hs Code.: 2933990090
• European Community (EC) Number: 840-798-5
• NSC Number: 25969
• DSSTox Substance ID: DTXSID90282454
• Nikkaji Number: J2.495.882E
• Wikidata: Q82016734
• ChEMBL ID: CHEMBL1410793
• Mol file: 5466-00-2.mol

Synonyms:5,6-trimethyleneuracil

Chemical Property of 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione

Chemical Property:

• Vapor Pressure: 6.38E-09mmHg at 25°C
• Melting Point: 328～330℃
• Boiling Point: 455.7°C at 760 mmHg
• Flash Point: 229.4°C
• PSA: 65.72000
• Density: 1.38g/cm³
• LogP: -0.44810
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), DMSO (Slightly, Sonicated)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 152.058577502
• Heavy Atom Count: 11
• Complexity: 268

Purity/Quality:

99% ^*data from raw suppliers

5,6-Trimethyleneuracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C1)NC(=O)NC2=O
• Uses: 5,6-Trimethyleneuracil can be used as VCP/p97 inhibitors.

Technology Process of 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione

There total 23 articles about 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione 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: 99.0%

methyl 2-ureidocyclopentene-1-carboxylate (1196101-51-5) → 6,7-dihydro-5H-cyclopenta[d]pyrimidine-2,4-diol (5466-00-2)

Guidance literature:

methyl 2-ureidocyclopentene-1-carboxylate; With water; sodium hydroxide; at 20 - 85 ℃;

With hydrogenchloride; In water; at 0 ℃; pH=0 - 1;

Reference yield: 97.24%

methyl 2-ureidocyclopentene-1-carboxylate (1196101-51-5) → 1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione (5466-00-2)

Guidance literature:

With sodium hydroxide; at 110 ℃; for 1.5h;

Reference yield: 92.0%

methyl 2-oxocyclopentane-1-carboxylate (10472-24-9,265317-94-0) + urea (57-13-6) → 1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione (5466-00-2)

Guidance literature:

With chloro-trimethyl-silane; In N,N-dimethyl-formamide; at 0 - 20 ℃;

upstream raw materials:

2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one

2-amino-6,7-dihydro-3H-cyclopenta[d]pyrimidin-4(5H)-one

2-ethoxycarbonyl-1-cyclopentanone

urea

Downstream raw materials:

5,6-trimethylene-1,3-dimethyluracil

(S)-CPW 399

4-(2-(3-fluoro-4-methoxyphenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)benzoic acid methyl ester

2-(4-(2-(thiazol-5-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yloxy)phenyl)acetic acid methylester

Refernces

• 1、 Papoyan,Khachatryan,Panosyan,Kochikyan. "Synthesis of new 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione derivatives containing the substituted aliphatic ring". . . Retrieved 2012.
• 2、 Zhang, Yonglei,Xie, Xiaomin,Wang, Xueyuan,Wen, Tiantian,Zhao, Chi,Liu, Hailong,Zhao, Bo,Zhu, Yongqiang. "Discovery of novel pyrimidine molecules containing boronic acid as VCP/p97 Inhibitors". . . Retrieved 2021/04/12.
• 3、 -. "Synthetic method of medical intermediate cycloalkanopyrimidinedione compound". . . Retrieved 2020/12/15.