Potassium Carbonate → HCID 118364750, compound

HRID 1478598Notes

Reaction equation

HRID 1478598 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[N:26][N:27]([CH3:29])[CH:28]=5)=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:36][CH2:37][CH2:38][N:39]1[CH:43]=[CH:42][C:41](B2OC(C)(C)C(C)(C)O2)=[N:40]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:29][N:27]1[CH:28]=[C:24]([C:21]2[N:20]=[C:19]3[N:15]([CH2:14][CH:10]4[CH2:11][CH2:12][CH2:13][N:8]([C:5]5[N:4]=[CH:3][C:2]([C:41]6[CH:42]=[CH:43][N:39]([CH2:38][CH2:37][O:36][CH:31]7[CH2:32][CH2:33][CH2:34][CH2:35][O:30]7)[N:40]=6)=[CH:7][N:6]=5)[CH2:9]4)[N:16]=[N:17][C:18]3=[N:23][CH:22]=2)[CH:25]=[N:26]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 73507292HCID 73507292, compoundHCID 131330026HCID 131330026, compound

Product 1

HCID 118364750HCID 118364750, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1-((1-(5-bromopyrimidin-2-yl)piperidin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (30 mg, 0.066 mmol), 1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazole (32 mg, 0.099 mmol), Pd(dppf)2Cl2(2.7 mg, 0.003 mmol), and K2CO3(28 mg, 0.20 mmol) were dissolved in dioxane (1.2 ml)+H2O (0.3 ml), and the mixture was degassed with N2(gas), followed by stirring at 80° C. for 2 hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:20), to give 6-(1-methyl-1H-pyrazol-4-yl)-1-((1-(5-(1-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethyl)-1H-pyrazol-3-yl)pyrimidin-2-yl)piperidin-3-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (28 mg, 78%).

Workup

  1. customthe mixture was degassed with N2(gas)
  2. customAfter the completion of the reaction
  3. extractionthe reaction mixture was extracted with H2O, EA, and brine
  4. customby drying
  5. filtration(Na2SO4), filtration, and concentration under reduced pressure
  6. customthe residue was purified by column chromatography (MeOH:MC=1:20)

Sources & evidence

ORD record
ord-48caa82b87904da5923c79dc73dbb2b3
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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