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5-Fluoropyrimidine-4,6-diol

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5-Fluoropyrimidine-4,6-diol Basic information

Product Name:
5-Fluoropyrimidine-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
  • 5-fluoro-6-hydroxy-3,4-dihydropyrimidin-4-one
  • 5-FLUORO-PYRIMIDINE-4,6-DIOL ISO 9001:2015 REACH
CAS:
106615-61-6
MF:
C4H3FN2O2
MW:
130.08
Product Categories:
  • Fluorine series
  • PYRIMIDINE
Mol File:
106615-61-6.mol
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5-Fluoropyrimidine-4,6-diol Chemical Properties

Density 
1.73±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
pka
3.42±0.10(Predicted)
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Safety Information

HazardClass 
IRRITANT
HS Code 
29335990
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5-Fluoropyrimidine-4,6-diol Usage And Synthesis

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

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