Ethyl Acetate → HCID 53468672, compound

HRID 2401170Notes

Reaction equation

HRID 2401170 reaction equation
Br[C:2]1[C:3]([NH2:18])=[N:4][C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[N:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O1CCOCC1.O>[CH3:19][N:20]1[CH:24]=[C:23]([C:2]2[C:3]([NH2:18])=[N:4][C:5]([N:13]3[CH:17]=[CH:16][CH:15]=[N:14]3)=[N:6][C:7]=2[N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:22]=[N:21]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 534669585-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine

Product 1

HCID 53468672HCID 53468672, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.1 g (0.33 mmol) of 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine (Example 1), 0.10 g (0.49 mmol) of 1-methylpyrazole-4-boronic acid pinacol ester, 0.23 (0.72 mmol) of cesium carbonate and 5 mg (6.5 μmol) of [1,1′-Bis(diphenylphosphino) ferrocene]dichloropaladium (II) dichloromethane complex in 3 ml dioxane and 0.5 ml of water were irradiated with microwaves at 140° C. for 30 min. After cooling to room temperature ethyl acetate was added and filtered by celite. The solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine. The organic layer was separated, dried with MgSO4 and concentrated. The residue was purified by column chromatography with silica gel and methylene chloride and methanol as eluent to give 45.5 mg (45.3%) of the desired product.

Workup

  1. customwere irradiated with microwaves at 140° C. for 30 min
  2. additionwas added
  3. filtrationfiltered by celite
  4. extractionThe solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography with silica gel and methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-a1288cb7cdbf4a73815657f5c4b9cf6a
Source dataset
uspto-grants-2014_08
Patent number
US08796284B2

Reaction notes

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