5-Chloro-6-(chloromethyl)pyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 5-Chloro-6-(chloromethyl)pyrimidine-2,4(1H,3H)-dione
• CAS No.: 73742-45-7
• Molecular Formula: C5H4 Cl2 N2 O2
• Molecular Weight: 195.005
• Hs Code.: 2933599090
• European Community (EC) Number: 814-407-3
• DSSTox Substance ID: DTXSID70400235
• Nikkaji Number: J3.207.491J
• Wikidata: Q82203105
• Mol file: 73742-45-7.mol

Synonyms:73742-45-7;5-Chloro-6-(chloromethyl)pyrimidine-2,4(1H,3H)-dione;5-chloro-6-(chloromethyl)-1H-pyrimidine-2,4-dione;5-chloro-6-(chloromethyl)-2,4(1H,3H)-Pyrimidinedione;5-chloro-6-chloromethyluracil;5-chloro-6-(chloromethyl)uracil;2,4(1H,3H)-Pyrimidinedione, 5-chloro-6-(chloromethyl)-;5-chloro-6-(chloromethyl)pyrimidine-2,4-diol;5-Chloro-6-chloromethyl-1H-pyrimidine-2,4-dione;2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI);5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione;5-chloro-6-chloromethyl-uracil;SCHEMBL6060121;DTXSID70400235;BXVCXZREYQLVTA-UHFFFAOYSA-N;AMY25408;BCP19522;YCA74245;MFCD01571383;AKOS006229242;AKOS037646747;SB38510;AS-70623;CS-0008571;FT-0685712;W16813;J-517371

Chemical Property of 5-Chloro-6-(chloromethyl)pyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Melting Point: 270-275 °C (decomp)
• Refractive Index: 1.583
• PKA: 5.73±0.10(Predicted)
• PSA: 65.72000
• Density: 1.63g/cm³
• LogP: 0.45540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 193.9649828
• Heavy Atom Count: 11
• Complexity: 249

Purity/Quality:

98%min ^*data from raw suppliers

5-Chloro-6-(chloromethyl)pyrimidine-2,4(1H,3H)-dione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1=C(C(=O)NC(=O)N1)Cl)Cl

Technology Process of 5-Chloro-6-(chloromethyl)pyrimidine-2,4(1H,3H)-dione

There total 18 articles about 5-Chloro-6-(chloromethyl)pyrimidine-2,4(1H,3H)-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: 94.0%

6-chloromethyluracil (18592-13-7) → 5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (73742-45-7)

Guidance literature:

With N-chloro-succinimide; In N,N-dimethyl-formamide; at 60 ℃; for 3h; Temperature; Solvent; Reagent/catalyst;

Reference yield: 92.0%

5-chloro-6-(hydroxymethyl)-2 4-(1H,3H)-pyrimidinedione → 5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (73742-45-7)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; Reflux;

Reference yield: 92.0%

→ 5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (73742-45-7) + 5-chloro-6-N-methylaminomethyluracil (183205-18-7)

Guidance literature:

upstream raw materials:

5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil

hydrogenchloride

6-chloromethyluracil

6-Methyluracil

Downstream raw materials:

5-chloro-6-methyluracil

Tipiracil

Refernces

• 1、 Cole, Christian,Reigan, Philip,Gbaj, Abdul,Edwards, Philip N.,Douglas, Kenneth T.,Stratford, Ian J.,Freeman, Sally,Jaffar, Mohammed. "Potential tumor-selective nitroimidazolylmethyluracil prodrug derivatives: Inhibitors of the angiogenic enzyme thymidine phosphorylase". . p. 207 - 209. Retrieved 2003.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF TIPIRACIL HYDROCHLORIDE AND INTERMEDIATES THEREOF". Page/Page column 11-12. . Retrieved 2020/07/07.
• 3、 -. "SUBSTITUTED PYRROLOPYRIDINES AS ATR INHIBITORS". Page/Page column 32. . Retrieved 2019/04/10.