Potassium Carbonate → HCID 67224108, compound

HRID 1257912Notes

Reaction equation

HRID 1257912 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([NH:11][CH3:12])=[O:10])=[C:4]([F:14])[CH:3]=1.CC1(C)C(C)(C)OB([C:23]2[CH:24]=[N:25][C:26]([NH2:29])=[N:27][CH:28]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O1CCOCC1.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>[NH2:29][C:26]1[N:27]=[CH:28][C:23]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([NH:11][CH3:12])=[O:10])=[C:4]([F:14])[CH:3]=2)=[CH:24][N:25]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 67223969HCID 67223969, compound

Product 1

HCID 67224108HCID 67224108, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-bromo-2-fluorophenyl)-2-hydroxy-N-methylacetamide (0.4 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.11 g, 0.48 mmol), tetrakis(triphenylphosphine)palladium (0.01 g, 0.01 mmol) and potassium carbonate (0.16 g, 1.2 mmol) in toluene (0.6 mL) and 1,4-dioxane (0.6 mL) was heated at 100° C. for 1.5 h. After cooling to RT, the mixture was filtered through a pad of silica gel, washed with 10% methanol in dichloromethane. The filtrate was concentrated under reduced pressure and the residue purified by chromatography on silica gel with 10% methanol in dichloromethane to afford the desired product. LCMS: (M+H)=277.0.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe mixture was filtered through a pad of silica gel
  3. washwashed with 10% methanol in dichloromethane
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue purified by chromatography on silica gel with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-2a86878764334d98a3d51dbc3e973413
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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