Phosphorus oxychloride → 4-Chloro-5-phenyl-2-pyridin-2-ylpyrimidine

HRID 1674674Notes

Reaction equation

HRID 1674674 reaction equation
[C:1]1([C:7]2[C:8](O)=[N:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)([Cl:22])=O>CC#N>[Cl:22][C:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517493HCID 178517493, compound

Product 1

HCID 249037084-Chloro-5-phenyl-2-pyridin-2-ylpyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Phenyl-2-pyridin-2-ylpyrimidin-4-ol (4-1; 206 mg, 0.826 mmol) was stirred in 4 ml of anhydrous MeCN. Phosphorous oxychloride (0.077 ml, 0.83 mmol) was added and the resulting mixture was heated to reflux. After 1 h the reaction was cooled and concentrated in vacuo and quenched with half-saturated aqueous NaHCO3. The mixture was extracted 3× with DCM. The combined organic phases was dried over Na2SO4, filtered and concentrated to provide 4-chloro-5-phenyl-2-pyridin-2-ylpyrimidine (4-2). 1H NMR (CDCl3): δ 8.88 (s, 1H), 8.84 (s, 1H), 8.57 (d, J=8.0 Hz, 1H), 7.90 (dt, J=1.5, 7.6 Hz, 1H), 7.53 (m, 5H), 7.46 (dd, J=4.9, 7.1 Hz, 1H).

Workup

  1. temperaturethe resulting mixture was heated to reflux
  2. temperatureAfter 1 h the reaction was cooled
  3. concentrationconcentrated in vacuo
  4. customquenched with half-saturated aqueous NaHCO3
  5. extractionThe mixture was extracted 3× with DCM
  6. dry with materialThe combined organic phases was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-17ffb1cbb25a4b689615370126d88d2e
Source dataset
uspto-grants-2011_08
Patent number
US08003643B2

Reaction notes

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