106615-61-6

Basic information

• Product Name: 5-FLUORO-PYRIMIDINE-4,6-DIOL
• Synonyms: 5-FLUORO-PYRIMIDINE-4,6-DIOL;4(1H)-Pyrimidinone, 5-fluoro-6-hydroxy- (9CI);5-Fluoro-4,6-dihydroxypyrimidine ;4,6-Dihydroxy-5-fluoropyrimidine;4(3H)-PyriMidinone, 5-fluoro-6-hydroxy-;5-fluoro-6-hydroxypyriMidin-4(3H)-one
• CAS NO: 106615-61-6
• Molecular Formula: C4H3FN2O2
• Molecular Weight: 130.0772232
• Product Categories: PYRIMIDINE;Fluorine series
• Mol File: 106615-61-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 295.4 °C at 760 mmHg
• Flash Point: 132.4 °C
• Appearance: /
• Density: 1.73 g/cm³
• Vapor Pressure: 0.000869mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: 2-8°C
• PKA: 3.42±0.10(Predicted)
• CAS DataBase Reference: 5-FLUORO-PYRIMIDINE-4,6-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-PYRIMIDINE-4,6-DIOL(106615-61-6)
• EPA Substance Registry System: 5-FLUORO-PYRIMIDINE-4,6-DIOL(106615-61-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 106615-61-6(Hazardous Substances Data)

Usage

Uses

5-Fluoropyrimidine-4,6-diol is used in preparation of Phenylpyrimidine derivatives and analogs for use as Kynurenine-3-monooxygenase inhibitors.

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

InChI:InChI=1/C4H3FN2O2/c5-2-3(8)6-1-7-4(2)9/h1H,(H2,6,7,8,9)

Upstream product

• 685-88-1 fluoromalonic acid diethyl ester 
• 3473-63-0 formamidine acetic acid 
• 77287-34-4 formamide 
• 6313-33-3 formamidine hydrochloride 

Relevant articles and documents

Fluorine gas for life science syntheses: Green metrics to assess selective direct fluorination for the synthesis of 2-fluoromalonate esters

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

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

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.