Triphenylphosphine → HCID 24854608, compound

HRID 2102836Notes

Reaction equation

HRID 2102836 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:30][C:31]1[CH:32]=[CH:33][C:34]([O:40][CH3:41])=[C:35](B(O)O)[CH:36]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([Cl:10])[C:5]([Cl:9])=[C:6]([C:33]2[CH:32]=[C:31]([Cl:30])[CH:36]=[CH:35][C:34]=2[O:40][CH3:41])[N:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 156902,4,5,6-TetrachloropyrimidineHCID 62657Potassium Phosphate, TribasicHCID 27357515-Chloro-2-methoxyphenylboronic acid

Product 1

HCID 24854608HCID 24854608, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

In a 250 mL three-neck flask fitted with a degassing tube and temperature probe, acetonitrile (100 mL) and water (25 mL) were degassed with N2 for 30 min while stirring. 2,4,5,6-Tetrachloropyrimidine (8.77 g, 0.0402 mol, 1.5 equiv) and triphenylphosphine (0.70 g, 2.6 mmol, 0.1 equiv) were added and the resulting mixture was degassed for 15 min. 5-Chloro-2-methoxy-phenylboronic acid (5.00 g, 0.0268 mol, 1.0 equiv), K3PO4 (11.39 g, 0.0536 mol, 2.0 equiv) and palladium acetate (301 mg, 1.3 mmol, 0.05 equiv) were added and the resulting mixture was degassed for 5 min. After 2 h at rt, the reaction mixture was poured into CH2Cl2 (250 mL) and washed twice with water (125 mL). The organic layer was dried and concentrated. The crude product was purified by FCC to give a white solid (5.97 g, 69%). MS (ESI+): mass calcd. for C11H7Cl4N2O, 322.9; m/z found, 323.0 [M+H+]. 1H NMR (CDCl3): 7.45 (dd, J=8.9, 2.6 Hz, 1H), 7.31 (d, J=2.6 Hz, 1H), 6.94 (d, J=8.9 Hz, 1H), 3.82 (s, 3H).

Workup

  1. customIn a 250 mL three-neck flask fitted with a degassing tube
  2. customtemperature probe, acetonitrile (100 mL) and water (25 mL) were degassed with N2 for 30 min
  3. customthe resulting mixture was degassed for 15 min
  4. customthe resulting mixture was degassed for 5 min
  5. additionthe reaction mixture was poured into CH2Cl2 (250 mL)
  6. washwashed twice with water (125 mL)
  7. customThe organic layer was dried
  8. concentrationconcentrated
  9. customThe crude product was purified by FCC

Sources & evidence

ORD record
ord-1e0063cb1d3949ef80f10a9b293cfdf3
Source dataset
uspto-grants-2009_08
Patent number
US07576092B2

Reaction notes

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