Phosphorus oxychloride → Ethyl 2-(4-chloropyrimidin-5-YL)acetate

HRID 1473129Notes

Reaction equation

HRID 1473129 reaction equation
O=[C:2]1[NH:7][CH:6]=[N:5][CH:4]=[C:3]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].O=P(Cl)(Cl)[Cl:16]>O>[Cl:16][C:2]1[C:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 46856292Ethyl 2-(6-oxo-1,6-dihydropyrimidin-5-yl)acetate

Product 1

HCID 46856293Ethyl 2-(4-chloropyrimidin-5-YL)acetateYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 2-(6-oxo-1,6-dihydropyrimidin-5-yl)acetate (I107) (0.868 g, 4.77 mmol) was added POCl3 (6 mL) under an atmosphere of nitrogen and the resulting mixture was heated to reflux for 5 minutes and then cooled to room temperature. The reaction was slowly added to water (300 mL), the aqueous solution was extracted with DCM (3×100 mL), the combined organics were washed with brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound (I108) (0.885 g, 93% yield) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 8.61 (s, 1H), 4.21 (q, J=7.1 Hz, 2H), 3.76 (s, 2H), 1.28 (t, J=7.1 Hz, 3H). LCMS Method C: rt 5.09 min; m/z 201.1, 203.1 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 5 minutes
  3. extractionthe aqueous solution was extracted with DCM (3×100 mL)
  4. washthe combined organics were washed with brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-897e4406c5c54d2487a033abe5e97b2a
Source dataset
uspto-grants-2015_04
Patent number
US09012461B2

Reaction notes

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