Gimeracil

Base Information

• Chemical Name: Gimeracil
• CAS No.: 103766-25-2
• Molecular Formula: C5H4ClNO2
• Molecular Weight: 145.545
• Hs Code.: 29337900
• Mol file: 103766-25-2.mol

Synonyms:5-Chloro-2,4-dihydroxypyridine;5-Chloro-4-hydroxy-2(1H)-pyridinone;5-Chloro-4-hydroxy-2-pyridone;2(1H)-Pyridinone, 5-chloro-4-hydroxy-;Gimestat;Cdhp compound;

Chemical Property of Gimeracil

Chemical Property:

• Vapor Pressure: 0.000408mmHg at 25°C
• Melting Point: 274 ºC
• Refractive Index: 1.617
• Boiling Point: 281.9 ºC at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 124.3 ºC
• PSA: 53.09000
• Density: 1.56 g/cm³
• LogP: 0.73390
• Storage Temp.: Refrigerator
• Solubility.: Soluble in DMSO (up to 5 mg/ml).

Purity/Quality:

99% ^*data from raw suppliers

CDH3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,C
• Hazard Codes: F,C
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Gimeracil (103766-25-2) is a dihydropyrimidine dehydrogenase (DPD) inhibitor.? DPD is involved in the degradation of pyrimidine-based chemotherapeutic drugs such as 5-fluorouracil (5-FU).? Gimeracil is used along with 5-FU or Tegafur to prolong circulating concentrations of the drugs.1,2? Gimeracil has also been shown to act as a radiosensitizer via inhibition of homologous recombination in the repair of DNA double strand breaks.3
• Uses: Gimeracil is an inhibitor of dihydropyrimidine dehydrogenase, which inhibits the early step in homologous recombination for double strand breaks repair. Gimeracil is an antitumor agent. Gimeracil is a potent inhibitor of dihydropyrimidine dehydrogenase (DPD). Antitumor agent. A potent inhibitor of dihydropyrimidine dehydrogenase (DPD)

Technology Process of Gimeracil

There total 15 articles about Gimeracil 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: 93.2%

4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (21642-98-8) → 5-chloro-4-hydroxy-2(1H)-pyridinone (103766-25-2)

Guidance literature:

With hydrogen bromide; for 18h; Concentration; Reflux;

Reference yield: 93.0%

5-chloro-3-cyano-4-methoxy-2(1H)-pyridinone (147619-40-7) → 5-chloro-4-hydroxy-2(1H)-pyridinone (103766-25-2)

Guidance literature:

With hydrogen bromide; for 24h; Heating;

DOI:10.3987/COM-92-6195

Reference yield: 86.0%

3,5-dichloro-2,4-dihydroxypyridine (103792-80-9) → 5-Chloro-2,4-dihydroxypyridine (103766-25-2)

Guidance literature:

With acetic acid; sodium iodide; In acetonitrile; at 60 ℃; for 8h;

DOI:10.3184/174751918X15166150010920

upstream raw materials:

4,5-dichloro-2-hydroxypyridine

sodium ethanolate

3,5-dichloro-2,4-dihydroxypyridine

2,4-diethoxy-5-chloro-pyridine

Downstream raw materials:

2,3,5-trichloropyridine

2,4-dibromo-5-chloropyridine

4-(5-chloro-4-hydroxy-2-oxo-2H-pyridin-1-ylmethyl)-3-fluoro-benzonitrile

3-{3-[4-hydroxy-5-chloro-2-pyridyloxycarbonyl]benzoyl}-1-ethoxymethyl-5-fluorouracil

Refernces

• 1、 -. "Halo hydroxy aromatic compound,". Paragraph 0045. . Retrieved 2021/10/13.
• 2、 -. "A lucky US pyrimidine of the composition and its preparation method". Paragraph 0025; 0041; 0042; 0043; 0044; 0045. . Retrieved 2017/08/02.