Potassium Carbonate → HCID 58941092, compound

HRID 506868Notes

Reaction equation

HRID 506868 reaction equation
[CH3:1][O:2][C:3]1[C:8](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][N:4]=1.Cl[C:40]1[CH:45]=[CH:44][N:43]=[C:42]([NH:46][CH3:47])[N:41]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:1][O:2][C:3]1[C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[CH2:19][CH2:18]3)=[CH:15][CH:16]=2)=[CH:7][C:6]([C:40]2[CH:45]=[CH:44][N:43]=[C:42]([NH:46][CH3:47])[N:41]=2)=[CH:5][N:4]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 123976804-Chloro-N-methylpyrimidin-2-amineHCID 58941095HCID 58941095, compound

Product 1

HCID 58941092HCID 58941092, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To tert-butyl 4-(4-((E)-2-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)vinyl)phenyl)piperazine-1-carboxylate (191 mg, 0.37 mmol) and 4-chloro-N-methylpyrimidin-2-amine (79 mg, 0.55 mmol) in toluene (4 mL) and ethanol (2 mL) under nitrogen was added 2M aqueous potassium carbonate (0.55 mL, 1.10 mmol) followed by palladium tetrakis(triphenylphosphine) (17 mg, 14.6 μmol). The reaction mixture was heated at 120° C. overnight. The reaction mixture was partitioned between EtOAc (30 mL) and water (50 mL). The organic layer was dried (MgSO4), filtered and concentrated and the residue was purification by column chromatography (EtOAc) to give the title compound (168 mg, 91%) as a yellow solid.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (30 mL) and water (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurification by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-e0b2b2716a2d4369bbcee75f25321e8a
Source dataset
uspto-grants-2010_08
Patent number
US07786120B2

Reaction notes

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