Potassium Carbonate → 1571903-56-4

HRID 1478608Notes

Reaction equation

HRID 1478608 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12]C[C@H: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.[CH3:30][N:31]1[CH2:36][CH2:35][N:34]([CH2:37][C:38]2[CH:43]=[CH:42][C:41](B3OC(C)(C)C(C)(C)O3)=[CH:40][CH:39]=2)[CH2:33][CH2:32]1.C([O-])([O-])=[O:54].[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][C@H:10]4[O:54][CH2:12][CH2:13][N:8]([C:5]5[N:4]=[CH:3][C:2]([C:41]6[CH:40]=[CH:39][C:38]([CH2:37][N:34]7[CH2:33][CH2:32][N:31]([CH3:30])[CH2:36][CH2:35]7)=[CH:43][CH:42]=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 467390391-Methyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazineHCID 118364803HCID 118364803, compound

Product 1

HCID 735047191571903-56-4Yield 71%

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

(S)-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 (250 mg, 0.55 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzyl)piperazine (210 mg, 0.66 mmol), Pd(dppf)2Cl2 (23 mg, 0.027 mmol), and K2CO3 (228 mg, 1.65 mmol) were dissolved in dioxane (6 ml)+H2O (1.5 ml), and then degassed with N2 (gas), followed by stirring at 80° C. for 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=1:10), to give (S)-2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)pyrimidin-2-yl)morpholine (210 mg, 71%).

Workup

  1. customdegassed 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=1:10)

Sources & evidence

ORD record
ord-12873f22ccd64361b1fa3097a4c117c3
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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