Toluene → HCID 58938612, compound

HRID 598076Notes

Reaction equation

HRID 598076 reaction equation
[CH2:1]([CH:3]([CH2:26][CH3:27])[CH2:4][N:5]1[C:14]2[C:9](=[C:10](OS(C(F)(F)F)(=O)=O)[CH:11]=[CH:12][CH:13]=2)[C:8](=[O:23])[N:7]([CH3:24])[C:6]1=[O:25])[CH3:2].[CH3:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][C:30]=1OB(O)O.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>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>[CH3:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[CH:31][C:30]=1[C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8](=[O:23])[N:7]([CH3:24])[C:6](=[O:25])[N:5]2[CH2:4][CH:3]([CH2:26][CH3:27])[CH2:1][CH3:2]

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 22237849HCID 22237849, compoundHCID 86613886HCID 86613886, compound

Product 1

HCID 58938612HCID 58938612, compoundYield 42.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of [1-(2-ethylbutyl)-3-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-5-yl]-trifluoromethanesulfonate (29 mg, 0.071 mmol), 2,4-dimethylphenylboroic acid (21 mg, 0.14 mmol) and potassium carbonate (20 mg, 0.14 mmol) and toluene (2 ml) was added of tetrakis(triphenylphosphine)palladium(0) (41 mg, 0.036 mmol). The mixture was stirred at 90° C. for 18 h and diluted with water. The aqueous solution was extracted with ethyl acetate. The extract was washed with saturated sodium bicarbonate solution in water, 10% citric acid solution in water and brine, dried over magnesium sulfate, and concentrated under vacuum. The residue was purified by column chromatography eluting with 5% ethyl acetate/n-hexane to afford 11 mg (41%) the title compound.

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. washThe extract was washed with saturated sodium bicarbonate solution in water, 10% citric acid solution in water
  3. dry with materialbrine, dried over magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography
  6. washeluting with 5% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-b8d04ad7c8e74c79b75ad712e36a9150
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

Loading…