106615-61-6 Usage
Description
5-FLUORO-PYRIMIDINE-4,6-DIOL is an organic compound with the molecular formula C4H3FN2O2. It is a derivative of pyrimidine, a heterocyclic compound with diverse applications in various fields due to its unique chemical properties. The presence of a fluorine atom at the 5th position and two hydroxyl groups at the 4th and 6th positions contribute to its reactivity and potential uses in chemical synthesis and pharmaceutical applications.
Uses
Used in Pharmaceutical Industry:
5-FLUORO-PYRIMIDINE-4,6-DIOL is used as a key intermediate in the synthesis of Phenylpyrimidine derivatives and analogs. These compounds are known for their potential as Kynurenine-3-monooxygenase (KMO) inhibitors. KMO is an enzyme involved in the kynurenine pathway, which is a crucial metabolic route in the human body. Inhibition of KMO has been linked to the treatment of various neurological disorders, such as schizophrenia, Alzheimer's disease, and Parkinson's disease, as well as certain autoimmune diseases.
In the synthesis of Phenylpyrimidine derivatives, 5-FLUORO-PYRIMIDINE-4,6-DIOL serves as a building block, providing the necessary structural features for the development of potent and selective KMO inhibitors. These inhibitors can modulate the kynurenine pathway, potentially leading to therapeutic benefits in the treatment of the aforementioned conditions.
Furthermore, the unique chemical properties of 5-FLUORO-PYRIMIDINE-4,6-DIOL may also allow for the development of other bioactive compounds with diverse applications in the pharmaceutical industry. Its reactivity and structural features can be exploited in the design and synthesis of novel drugs targeting various diseases and conditions.
Preparation
synthesis of 5-Fluoro-4,6-dihydroxypyrimidine: Formamidine acetate (2.06 g, 20 mmol) was added to the solution of sodium (1.38 g, 60 mmol) in anhydrous ethanol (40 mL) and the mixture was heated to reflux. Diethyl 2-fluoromalonate (3.20 g, 18 mmol) was added dropwise over 20 minutes and the mixture was heated at reflux for 6 h. After cooling to room temperature, the solution was evaporated to dryness, the residue was dissolved in water (20 mL), acidified with HCl (5 mL), the precipitate was filtered, washed with water (5 mL), ethanol (2 × 5 mL) and diethyl ether (2 × 5 mL). After drying in vacuo, 5-fluoro-4,6-dihydroxypyrimidine (1.50 g, 64%) was obtained as a brown powder. m.p.: >300 °C; ([M + H]+ , 131.0244, C4H4FN2O2 requires: [M]+ , 131.0257); IR (neat, cm-1 ) 3053, 2639, 1633, 1547, 1388, 1213; δH (DMSO d6, 400 MHz) 7.90 (1H, s, C-H), 12.38 (2H, bs, OH); δF (DMSO d6, 376 MHz): -178.06 (s); δC (DMSO d6, 100 MHz) 132.79 (d, 1 JCF 235.6, C-F), 144.46 (d, 4 JCF 7.7, C-H), 155.83 (d, 2 JCF 15.0, C-OH); m/z (ASAP) 131 (100%, [M + H]+ ).21a
Check Digit Verification of cas no
The CAS Registry Mumber 106615-61-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,6,6,1 and 5 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 106615-61:
(8*1)+(7*0)+(6*6)+(5*6)+(4*1)+(3*5)+(2*6)+(1*1)=106
106 % 10 = 6
So 106615-61-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H3FN2O2/c5-2-3(8)6-1-7-4(2)9/h1H,(H2,6,7,8,9)
106615-61-6Relevant articles and documents
Fluorine gas for life science syntheses: Green metrics to assess selective direct fluorination for the synthesis of 2-fluoromalonate esters
Harsanyi, Antal,Sandford, Graham
, p. 3000 - 3009 (2015)
Optimisation and real time reaction monitoring of the synthesis of 2-fluoromalonate esters by direct fluorination using fluorine gas is reported. An assessment of green metrics including atom economy and process mass intensity factors, demonstrates that the one-step selective direct fluorination process compares very favourably with established multistep processes for the synthesis of fluoromalonates.
Discovery of MK-8282 as a Potent G-Protein-Coupled Receptor 119 Agonist for the Treatment of Type 2 Diabetes
Neelamkavil, Santhosh F.,Stamford, Andrew W.,Kowalski, Timothy,Biswas, Dipshikha,Boyle, Craig,Chackalamannil, Samuel,Xia, Yan,Jayne, Charles,Neustadt, Bernard,Hao, Jinsong,Liu, Hong,Dai, Xing,Baker, Hana,Hawes, Brian,O'Neill, Kim,Tang, Huadong,Greenlee, William J.
supporting information, p. 457 - 461 (2018/05/23)
The ever-growing prevalence of type 2 diabetes in the world has necessitated an urgent need for multiple orally effective agents that can regulate glucose homeostasis with a concurrent reduction in body weight. G-Protein coupled receptor 119 (GPR119) is a GPCR target at which agonists have demonstrated glucose-dependent insulin secretion and shows beneficial effects on glycemic control. Herein, we describe our efforts leading to the identification of a potent, oral GPR-119 agonist, MK-8282, which shows improved glucose tolerance in multiple animal models and has excellent off-target profile. The key design elements in the compounds involved a combination of a fluoro-pyrimidine and a conformationally constrained bridged piperidine to impart good potency and efficacy.
Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof
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Page/Page column 37, (2015/11/24)
Certain chemical entities are provided herein. Also provided are pharmaceutical compositions comprising at least one chemical entity and one or more pharmaceutically acceptable vehicle. Methods of treating patients suffering from certain diseases and disorders responsive to the inhibition of KMO activity are described, which comprise administering to such patients an amount of at least one chemical entity effective to reduce signs or symptoms of the disease or disorder are disclosed. These diseases include neurodegenerative disorders such as Huntington's disease. Also described are methods of treatment include administering at least one chemical entity as a single active agent or administering at least one chemical entity in combination with one or more other therapeutic agents. Also provided are methods for screening compounds capable of inhibiting KMO activity.
