Water → HCID 58289757, compound

HRID 2088415Notes

Reaction equation

HRID 2088415 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:27]=[CH:28][CH:29]=2)[CH2:11][N:12]2[C:16]3=[N:17][C:18]([C:21]4[CH:22]=[N:23][N:24]([CH3:26])[CH:25]=4)=[CH:19][N:20]=[C:15]3[N:14]=[N:13]2)=[N:6][CH:7]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)[O:31]1.C([O-])(=O)C.[K+].O>C1COCC1.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:26][N:24]1[CH:25]=[C:21]([C:18]2[N:17]=[C:16]3[N:12]([CH2:11][C:10]4[CH:9]=[C:8]([C:5]5[N:4]=[CH:3][C:2]([OH:31])=[CH:7][N:6]=5)[CH:29]=[CH:28][CH:27]=4)[N:13]=[N:14][C:15]3=[N:20][CH:19]=2)[CH:22]=[N:23]1

Participants

8

Reactant 4

HCID 962WaterHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 58289778HCID 58289778, compound

Product 1

HCID 58289757HCID 58289757, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

800 mg (1.66 mmol) of 1-[3-(5-bromopyrimidin-2-yl)benzyl]-6-(1-methyl-1H-pyrazol-4-yl)-1H-1,2,3-triazolo[4,5-b]pyrazine is suspended in 10 ml of THF and 1 ml of DMF, and 515 mg (1.99 mmol) of bis(pinacolato)diboron and 488 mg (4.97 mmol) of potassium acetate are added. The reaction mixture is evacuated and flushed with argon a number of times. 16.3 mg (0.023 mmol) of bis(triphenylphosphine)palladium(II) chloride is added, and the mixture is again evacuated and flushed with argon. The reaction mixture is stirred at 80° C. for 24 h. When the reaction of the starting material is complete, 255 mg (1.656 mmol) of sodium perborate trihydrate and 2 ml of water are added to the reaction mixture, which is then stirred at room temperature for 24 h. The reaction mixture is filtered off with suction and washed with ethyl acetate. The filtrate is subsequently adjusted to pH 12 using NaOH solution and extracted with ethyl acetate. The aqueous phase is neutralised using hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases are then dried over sodium sulfate and evaporated under reduced pressure.

Workup

  1. customThe reaction mixture is evacuated
  2. customflushed with argon a number of times
  3. customthe mixture is again evacuated
  4. customflushed with argon
  5. customWhen the reaction of the starting material
  6. stirringis then stirred at room temperature for 24 h
  7. filtrationThe reaction mixture is filtered off with suction
  8. washwashed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. extractionextracted twice with ethyl acetate
  11. dry with materialThe combined organic phases are then dried over sodium sulfate
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fdb9feb4577c4e9ca64de95bb512e7c6
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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