Water → Methyl 4-(4-pyrimidinyl)benzoate

HRID 379555Notes

Reaction equation

HRID 379555 reaction equation
[CH3:1][O:2]BO.Cl.Cl[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][N:8]=1.[F-].[K+].[OH2:15].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[N:10]1[CH:11]=[CH:12][C:7]([C:19]2[CH:20]=[CH:21][C:16]([C:22]([O:2][CH3:1])=[O:15])=[CH:17][CH:18]=2)=[N:8][CH:9]=1

Participants

9

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 522689Potassium FluorideHCID 219225564-Chloropyrimidine hydrochlorideHCID 178486307HCID 178486307, compound

Product 1

HCID 22329706Methyl 4-(4-pyrimidinyl)benzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

1,1′-Bis(diphenylphosphino)ferrocene (2.48 g, 4.5 mmol) and palladium (II) acetate (1.0 g, 4.5 mmol) were stirred at 50° C. in toluene (25 ml) under an atmosphere of nitrogen for 30 minutes, then allowed to cool to room temperature. The boronic acid methyl ester from b) above (2.2 g, 11.2 mmol), 4-chloropyrimidine hydrochloride from a) above (1.69 g, 11.2 mmol) and potasium fluoride (3.9 g, 67 mmol) were added followed by water (25 mL). The reaction mixture was refluxed overnight under an atmosphere of nitrogen. The reaction mixture was separated between ethyl acetate (100 ml) and water (100 ml). The organic layer was dried over magnesium sulphate, filtered and concentrated in vacuo to yield a black oil which was subjected to chromatography (SiO2: 100% Ethyl acetate) to yield methyl 4-(4-pyrimidinyl)benzoate as a brown solid (1.17 g); 1H NMR (250 MHZ, DMSO-d6) δ=3.91 ppm (s,3H), δ8.13 & 8.36 ppm (dd,4H), δ=8.19 ppm (dd,1H), δ=8.94 ppm (d,1H), δ=9.32 ppm (d,1H); MS (M+H)+ 215.

Workup

  1. temperatureThe reaction mixture was refluxed overnight under an atmosphere of nitrogen
  2. customThe reaction mixture was separated between ethyl acetate (100 ml) and water (100 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a black oil which

Sources & evidence

ORD record
ord-fc7cf8e88c524f8aa6f504e85c9be462
Source dataset
uspto-grants-2001_10
Patent number
US06300330B1

Reaction notes

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