Potassium Carbonate → HCID 79073067, compound

HRID 1025957Notes

Reaction equation

HRID 1025957 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[Cl:17].C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.C(OCC)(=O)C.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:1][C:2]1[N:7]=[C:6]([C:14]2[CH:13]=[CH:12][C:11]([Cl:10])=[C:16]([Cl:17])[CH:15]=2)[C:5]([F:9])=[CH:4][N:3]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 27343303,4-Dichlorobenzeneboronic acid

Product 1

HCID 79073067HCID 79073067, compoundYield 74.13%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 20 g 2,4-dichloro-5-fluoropyrimidine, 22.86 g 3,4-dichlorophenylboronic acid, 33.11 g potassium carbonate and 6.92 g tetrakis(triphenylphosphine)palladium were in 500 mL THF and 500 mL water was heated to reflux for 4 h. The reaction mixture was cooled to room temperature diluted with water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel with dichloromethane to yield 24.640 g (74.13%) of the title compound as white solid, MS 279.1 (M+H)+.

Workup

  1. temperatureto reflux for 4 h
  2. customThe phases were separated
  3. customthe organic phase was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-f851fc362de647b49c0d009ac153d445
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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