Phosphorus oxychloride → HCID 178430308, compound

HRID 2170802Notes

Reaction equation

HRID 2170802 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[C:11]([CH3:15])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:18])=O>O>[Cl:18][CH:12]1[NH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:9][CH:10]=[C:11]1[CH3:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 599066112-(4-Chloro-phenyl)-5-methyl-3H-pyrimidin-4-one

Product 1

HCID 178430308HCID 178430308, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-Chloro-phenyl)-5-methyl-3H-pyrimidin-4-one (570 mg, 2.58 mmol) was suspended in phosphorus oxychloride (2 ml) and heated to reflux for 2 hours. The mixture was cooled before being stripped to dryness in vacuo. The resulting crude product was solubilised in water (10 ml) and ethyl acetate (10 ml) and the biphasic mixture separated. The aqueous layer was further extracted with ethyl acetate (10 ml) before the combined organics were dried with magnesium sulphate, filtered and stripped to dryness in vacuo to give 6-Chloro-2-(4-chloro-phenyl)-5-methyl-1,6-dihydro-pyrimidine as a white solid (567 mg, 2.38 mmol, 92% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. temperatureThe mixture was cooled
  4. customethyl acetate (10 ml) and the biphasic mixture separated
  5. extractionThe aqueous layer was further extracted with ethyl acetate (10 ml) before the combined
  6. dry with materialorganics were dried with magnesium sulphate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-70814a55b4ad43909d17efb6c68b6058
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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