Potassium Carbonate → HCID 67223283, compound

HRID 1257929Notes

Reaction equation

HRID 1257929 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:22]=[CH:21][C:11]([C:12]([NH:14][CH:15]([CH3:20])[C:16]([O:18]C)=[O:17])=[O:13])=[C:10]([F:23])[CH:9]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][C:35]([NH2:38])=[N:36][CH:37]=2)O1>O.C1(C)C=CC=CC=1.C(O)C.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>[NH2:38][C:35]1[N:36]=[CH:37][C:32]([C:8]2[CH:22]=[CH:21][C:11]([C:12]([NH:14][CH:15]([CH3:20])[C:16]([OH:18])=[O:17])=[O:13])=[C:10]([F:23])[CH:9]=2)=[CH:33][N:34]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 60675698HCID 60675698, compound

Product 1

HCID 67223283HCID 67223283, compoundYield 101.1%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of potassium carbonate (0.35 g, 2.5 mmol) in water (2 mL) was added to a mixture of methyl 2-[(4-bromo-2-fluorobenzoyl)amino]propanoate (0.5 g, 1.6 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (0.28 g, 1.3 mmol), and tetrakis(triphenylphosphine)palladium (0.07 g, 0.06 mmol) in toluene (4 mL) and ethanol (2 mL). The resulting mixture was heated at 120° C. for 15 min The reaction mixture was extracted with ether (3×10 mL) to remove impurity. The aqueous layer was adjusted to pH 7 with aqueous HCl and purified by RP-HPLC (pH 10) to afford the desired product (0.40 g, 100%). LCMS: (M+H)=305.0.

Workup

  1. extractionwas extracted with ether (3×10 mL)
  2. customto remove impurity
  3. custompurified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-edbd8efe3a224197ac53000f79c3c600
Source dataset
uspto-grants-2013_06
Patent number
US08461330B2

Reaction notes

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