Sodium Carbonate → HCID 117760267, compound

HRID 709816Notes

Reaction equation

HRID 709816 reaction equation
C[C:2]1[N:7]=[C:6]([C:8]#[N:9])[N:5]=[C:4]([O:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]=1Br.[F:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[C:3]1[C:4]([O:10][CH2:11][CH:12]([CH3:13])[CH3:14])=[N:5][C:6]([C:8]#[N:9])=[N:7][CH:2]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 117760014HCID 117760014, compound

Product 1

HCID 117760267HCID 117760267, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Under an argon atmosphere, to a solution of methyl 5-bromo-4-isobutoxypyrimidine-2-carbonitrile (1.71 g) in toluene (20 mL) were added 2-fluoro-5-methoxyphenylboronic acid (1.70 g), tris(dibenzylideneacetone)dipalladium(0) (245 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (439 mg) and 2.0 M aqueous sodium carbonate solution (10.0 mL), and the mixture was stirred at 80° C. for 1 hr. The reaction mixture was filtered through celite, and water was added at room temperature. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.78 g) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered through celite, and water
  2. additionwas added at room temperature
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe extract was washed with water and saturated brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c16a2aac1054416e9aff2d683eda835c
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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