Potassium Carbonate → HCID 57839072, compound

HRID 732955

Reaction equation

HRID 732955 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=C[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[C:20]([CH3:23])=[CH:21][CH:22]=1.[C:27]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:7]([CH:8]=[O:9])=[CH:2][N:3]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:5]=2)=[C:19]([CH3:27])[CH:18]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 57839061HCID 57839061, compound

Product 1

HCID 57839072HCID 57839072, compoundYield 88.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 4-chloro-2-phenylpyrimidine-5-carbaldehyde (50 mg, 0.23 mmol) and 4-chloro-o-toluene boronic acid (48 mg, 0.29 mmol) in dioxane (1 mL) and H2O (0.5 mL) was added Pd(PPh3)4 (26.5 mg, 0.02 mmol), K2CO3 (126.5 mg, 0.92 mmol). The reaction was heated to 85° C. for 6 hrs. After concentration under reduced pressure, the residue was diluted with EtOAc (10 mL) and the organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product (70 mg). The crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane) to give 4-(4-chloro-2-methylphenyl)-2-phenylpyrimidine-5-carbaldehyde (63 mg, 75%) as a white solid.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue was diluted with EtOAc (10 mL)
  3. washthe organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product (70 mg)
  8. customThe crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-d8a06cc992f54305bf7417ba9ab58325
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Linked notes

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