Ethyl Acetate → HCID 86626270, compound

HRID 1518485Notes

Reaction equation

HRID 1518485 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:9](/B(O)O)=[CH:10]\[CH3:11].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>C1(C)C=CC=CC=1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:8][C:5]1[N:4]=[CH:3][C:2](/[CH:9]=[CH:10]/[CH3:11])=[CH:7][N:6]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 6157276((1E)-prop-1-en-1-yl)boronic acid

Product 1

HCID 86626270HCID 86626270, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To 5-bromo-2-chloropyrimidine (2.027 g, 10.48 mmol), (E)-prop-1-enylboronic acid (1.350 g, 15.72 mmol), PdCl2(dppf)-CH2Cl2 (0.428 g, 0.524 mmol), and potassium carbonate (4.35 g, 31.4 mmol) in toluene (20 mL) and water (0.5 mL) was bubbled nitrogen subsurface for 1 minute and then placed in a 90° C. oil bath for 5 hours. 200 mL EtOAc was added and the reaction was then washed with 3×200 mL of water, dried with MgSO4, filtered and concentrated to 1.53 g brown solids. This was purified by flash chromatography (5% EtOAc in hexanes) to yield product (681 mg) as an off-white solid. MS (ESI) 155.7 (M+1).

Workup

  1. customplaced in a 90° C.
  2. customfor 5 hours
  3. washthe reaction was then washed with 3×200 mL of water
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to 1.53 g brown solids
  7. customThis was purified by flash chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-30fbfff8880340ed8aa29ad0c6ede3d6
Source dataset
uspto-grants-2012_07
Patent number
US08232404B2

Reaction notes

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