Phosphorus oxychloride → HCID 59846662, compound

HRID 2063608Notes

Reaction equation

HRID 2063608 reaction equation
[CH2:1]([C:3]1[NH:8][C:7](=O)[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[N:4]=1)[CH3:2].P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:7]1[CH:6]=[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])[N:4]=[C:3]([CH2:1][CH3:2])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136138320HCID 136138320, compound

Product 1

HCID 59846662HCID 59846662, compoundYield 74.7%

Procedure

A solution of 2-ethyl-6-(2-methoxy-phenyl)-3H-pyrimidin-4-one (1.1 g, 4.9 mmol) and phosphorous oxychloride (3.0 mL, 32 mmol) was refluxed for four hours. After cooling to ambient temperature the reaction mixture was concentrated in vacuo and the resultant residue was diluted with dichloromethane. The organics were washed with ice-water. After extraction of the aqueous layer with dichloromethane the combined organics were washed with brine and dried over sodium sulfate. Following Si gel chromatography (1:5 ethyl acetate:hexanes) 0.91 g (74%) of the title compound was isolated as a pale yellow oil.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionthe resultant residue was diluted with dichloromethane
  3. washThe organics were washed with ice-water
  4. extractionAfter extraction of the aqueous layer with dichloromethane the combined
  5. washorganics were washed with brine
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-19d102663d6c4aa3b5177d16432b841b
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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