Acetonitrile → HCID 67261970, compound

HRID 2359108Notes

Reaction equation

HRID 2359108 reaction equation
C(#N)C.C(=O)([O-])[O-].[K+].[K+].[Cl:10][C:11]1[S:15][C:14]([C:16]2[C:20](B3OC(C)(C)C(C)(C)O3)=[CH:19][N:18]([CH2:30][CH:31]([CH3:33])[CH3:32])[N:17]=2)=[CH:13][CH:12]=1.[NH2:34][C:35]1[CH:40]=[C:39](Cl)[N:38]=[CH:37][N:36]=1>O>[Cl:10][C:11]1[S:15][C:14]([C:16]2[C:20]([C:39]3[N:38]=[CH:37][N:36]=[C:35]([NH2:34])[CH:40]=3)=[CH:19][N:18]([CH2:30][CH:31]([CH3:32])[CH3:33])[N:17]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 2380124-Amino-6-chloropyrimidineHCID 67389116HCID 67389116, compound

Product 1

HCID 67261970HCID 67261970, compoundYield 5.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a degassed solution of acetonitrile (4 mL) and water (1 mL) were added potassium carbonate (4 eq, 2.8 mmol), 3-(5-chloro-2-thienyl)-1-isobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 eq, 0.7 mmol), 4-amino-6-chloropyrimidine (1.1 eq, 0.77 mmol) and 1,1′-bis(diphenylphosphinoferrocene)palladium(II)dichloride (0.1 eq, 0.07 mmol). The mixture was stirred at 130° C. in the microwave for 60 min. At room temperature, the mixture was filtered over celite and the filtrate was evaporated. The residue was purified by chromatography on silica gel (dichloromethane:methanol 1:0 to 9:1) to afford 12 mg of 6-[3-(5-chloro-2-thienyl)-1-isobutyl-1H-pyrazol-4-yl]pyrimidin-4-amine (5% yield).

Workup

  1. filtrationAt room temperature, the mixture was filtered over celite
  2. customthe filtrate was evaporated
  3. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol 1:0 to 9:1)

Sources & evidence

ORD record
ord-1bcb972693444429bbb8c6a0bbffe409
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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