Potassium Carbonate → tert-butyl[3-(2-aminopyrimidin-5-yl)-1H-pyrazol-1-yl]acetate

HRID 500271Notes

Reaction equation

HRID 500271 reaction equation
[NH:1]1[C:5](B(O)O)=[CH:4][CH:3]=[N:2]1.Br[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[C:25]1[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=1>CN(C)C=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>[C:14]([O:13][C:11](=[O:12])[CH2:10][N:2]1[CH:3]=[CH:4][C:5]([C:25]2[CH:26]=[N:27][C:28]([NH2:31])=[N:29][CH:30]=2)=[N:1]1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 2313102-Amino-5-bromopyrimidineHCID 112519791H-Pyrazole-5-boronic acid

Product 1

HCID 90849675tert-butyl[3-(2-aminopyrimidin-5-yl)-1H-pyrazol-1-yl]acetate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-pyrazol-5-ylboronic acid (0.2 g, 2 mmol) in N,N-dimethylformamide (1.0 mL) were added 1,1-dimethylethyl bromoacetate (0.38 g, 2 mmol) and potassium carbonate (0.74 g, 0.0054 mol). The reaction mixture was stirred overnight at RT. To the reaction mixture was added 5-bromopyrimidin-2-amine (0.40 g, 2.3 mmol) and tetrakis(triphenylphosphine)palladium (0.1 g, 0.09 mmol). The resulting mixture was stirred at 100° C. for 2 h. After cooling to RT, the reaction mixture was extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by RP-HPLC to afford the desired product. LCMS: (M+H)=276.0.

Workup

  1. stirringThe resulting mixture was stirred at 100° C. for 2 h
  2. temperatureAfter cooling to RT
  3. extractionthe reaction mixture was extracted with EtOAc (3×30 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-0f2b61a863b44e03adc46c6492ad2357
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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