Phosphorus oxychloride → 4-Methoxy-5-phenyl-2,6-bis-(4-pyridyl)-pyrimidine

HRID 398032Notes

Reaction equation

HRID 398032 reaction equation
[C:1]1([C:7]2[C:8](=[O:25])[NH:9][C:10]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)=O.Cl[C:32]1N=C(C2C=CN=CC=2)C(C2C=CC(F)=CC=2)=CN=1.ClC1C(C2C=CC=CC=2)=C(C2C=CN=CC=2)N=C(C2C=CN=CC=2)N=1.C[O-].[Na+]>CO>[CH3:32][O:25][C:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[N:11]=[C:10]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[N:9]=1

Participants

7

Reactant 5

HCID 24813Phosphorus oxychlorideHCID 10942334Sodium MethoxideHCID 230003652-Chloro-5-(4-fluorophenyl)-4-(4-pyridyl)-pyrimidineHCID 230004174-Chloro-5-phenyl-2,6-bis-(4-pyridyl)-pyrimidineHCID 1357030155-phenyl-2,6-bis-(4-pyridyl)-4(3H)-pyrimidinone

Product 1

HCID 230005214-Methoxy-5-phenyl-2,6-bis-(4-pyridyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-phenyl-2,6-bis-(4-pyridyl)-4(3H)-pyrimidinone (360 mg, 1.10 mmol) and phosphorus oxychloride (2 ml) was heated at reflux for 1.5 h. Work-up was done as described for the preparation of 2-chloro-5-(4-fluorophenyl)-4-(4-pyridyl)-pyrimidine. To a solution of the crude 4-chloro-5-phenyl-2,6-bis-(4-pyridyl)-pyrimidine (250 mg, 0.73 mmol) in methanol (5 ml) was added methanolic 0.5 N sodium methoxide (1.45 ml, 0.73 mmol) and it was heated at reflux for 1 h. After evaporation, the resultant material was partitioned between ethyl acetate and water. The organic solution was washed with water, dried and evaporated. Chromatography of the crude product on a column of silica gel (ethyl acetate) provided the title compound. MS (m/z): 341.2 (M+H)+; C21H16N4O requir. 340.4 1H-NMR (CDCl3): 8.82, 8.54, 8.40 (3 m, each 2H, Pyrid.), 7.40-7.18 (m, 7H, Ph, Pyrid.), 4.15 (s, 3H, CH3O).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 h
  3. temperaturewas heated
  4. temperatureat reflux for 1 h
  5. customAfter evaporation
  6. customthe resultant material was partitioned between ethyl acetate and water
  7. washThe organic solution was washed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-4afb6c41442649d7b6c41e8d8493b8c7
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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