Phosphorus oxychloride → HCID 114582250, compound

HRID 1526286Notes

Reaction equation

HRID 1526286 reaction equation
O[C:2]1[N:7]=[CH:6][N:5]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:4](=[O:14])[CH:3]=1.P(Cl)(Cl)([Cl:17])=O.C(=O)([O-])O.[Na+]>O>[Cl:17][C:2]1[N:7]=[CH:6][N:5]([CH:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[C:4](=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 137001376HCID 137001376, compound

Product 1

HCID 114582250HCID 114582250, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-hydroxy-3-(tetrahydro-2H-pyran-4-yl)pyrimidin-4(3H)-one obtained in Reference Example 25 (210 mg) and phosphorus oxychloride (6 mL) was stirred at 100° C. for 2 hr. The mixture was allowed to be cooled to room temperature, the solvent was evaporated under reduced pressure, and the residue was subjected to azeotropy with toluene to give a residue. The residue was dissolved in water (10 mL), and the solution was basified with saturated aqueous sodium hydrogen carbonate solution (30 mL) under ice-cooling. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give a residue. The residue was purified by chromatography (hexane/ethyl acetate) to give the title compound (125 mg).

Workup

  1. temperatureto be cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. customto give a residue
  4. temperaturecooling
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customto give a residue
  10. customThe residue was purified by chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5af403f51a0a42dd983b68d711f2b571
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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