| Identification | Back Directory | [Name]
5-FLUORO-PYRIMIDINE-4,6-DIOL | [CAS]
106615-61-6 | [Synonyms]
5-FLUORO-PYRIMIDINE-4,6-DIOL
4,6-Dihydroxy-5-fluoropyrimidine
5-Fluoro-4,6-dihydroxypyrimidine
5-fluoro-4-hydroxy-1H-pyrimidin-6-one
5-fluoro-6-hydroxypyriMidin-4(3H)-one
4(3H)-PyriMidinone, 5-fluoro-6-hydroxy-
4(1H)-Pyrimidinone, 5-fluoro-6-hydroxy- (9CI)
5-fluoro-6-hydroxy-3,4-dihydropyrimidin-4-one
5-FLUORO-PYRIMIDINE-4,6-DIOL ISO 9001：2015 REACH | [Molecular Formula]
C4H3FN2O2 | [MDL Number]
MFCD09033260 | [MOL File]
106615-61-6.mol | [Molecular Weight]
130.08 |
| Chemical Properties | Back Directory | [density ]
1.73±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
3.42±0.10(Predicted) | [Appearance]
Off-white to light brown Solid |
| Hazard Information | Back Directory | [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 | [Synthesis]
GENERAL STEPS: To a stirred solution of sodium ethanolate (2.7 g, 0.04 mol) in ethanol (40 mL) was added formamidine hydrochloride (4.2 g, 0.04 mol), followed by the slow dropwise addition of diethyl 2-fluoromalonate (dissolved in 10 mL of ethanol) at 0 °C. The reaction mixture was heated to 90 °C and stirred overnight. Upon completion of the reaction, ethanol was removed by distillation under reduced pressure and the residue was acidified with concentrated hydrochloric acid to pH < 2. The precipitated solid was collected by filtration and washed with a small amount of cold water, and finally dried under vacuum to afford 5-fluoro-4,6-dihydroxypyrimidine as crude product (750 mg, 52% yield). The structure of the product was confirmed by 1H-NMR (DMSO-d6, 200 MHz): δ 12.40 (broad peak, 2H, OH), 7.89 (single peak, 1H, pyrimidine ring H). | [References]
[1] Patent: US2009/36419, 2009, A1. Location in patent: Page/Page column 43; 44
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 5, p. 457 - 461 |
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