Water → HCID 58772825, compound

HRID 271454Notes

Reaction equation

HRID 271454 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:6]([Cl:14])[N:5]=[CH:4][N:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1(C)C=CC=CC=1.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:14][C:6]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[N:3]=[CH:4][N:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 58772827HCID 58772827, compound

Product 1

HCID 58772825HCID 58772825, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 4,6-dichloro-5-(pyridin-4-yl)pyrimidine (1.07 g, 4.8 mmol), 4-chlorophenylboronic acid (740 mg, 4.8 mmol) and tetrakis(triphenylphosphine)palladium (550 mg, 0.48 mmol) in toluene (10 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 5 mL, 10 mmol). The resulting mixture was stirred at 100° C. under argon for 15 h. Analysis by HPLC/MS indicated that the reaction was complete. After the reaction mixture was cooled to room temperature, water (25 mL) was added. The resulting mixture was extracted with EtOAc (2×25 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain the title compound (1.12 g, HPLC purity about 92%) as a white solid. 1H NMR (CDCl3): δ7.18 (d, 2H), 7.2-7.3 (m, 4H), 8.66 (d, 2H), 9.07 (s, 1H).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionThe resulting mixture was extracted with EtOAc (2×25 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluted with ethyl acetate-hexanes

Sources & evidence

ORD record
ord-9493d09e377a4fd2ab0795e558f38775
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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