Potassium Acetate → HCID 58477157, compound

HRID 1043752Notes

Reaction equation

HRID 1043752 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][C:12]2[N:16]3[CH: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+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:26][N:24]1[CH:25]=[C:21]([C:18]2[CH:19]=[N:20][C:15]3[N:16]([C: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]=3)[CH:17]=2)[CH:22]=[N:23]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 58477185HCID 58477185, compound

Product 1

HCID 58477157HCID 58477157, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

4.03 g of 3-[3-(5-bromopyrimidin-2-yl)benzyl]-6-(1-methyl-1H-pyrazol-4-yl)-1,2,4-triazolo[4,3-a]pyrimidine are suspended in 18 ml of THF, heated to 80° C., and 2.86 g of bis(pinacolato)diboron, 2.65 g of potassium acetate and 126 mg of bis(triphenylphosphine)palladium(II)chloride are added and refluxed at 80° C. for 4 h [RM1]. The hot RM is filtered off with suction, rinsed with THF and evaporated to about 30 ml. 30 ml of water and 1.52 g of sodium perborate are then added and stirred at RT overnight. The mixture is acidified using 1 N HCl, THF is distilled off, the precipitate formed is filtered off with suction, washed with water, sucked dry and dried.

Workup

  1. temperaturerefluxed at 80° C. for 4 h [RM1]
  2. filtrationThe hot RM is filtered off with suction
  3. washrinsed with THF
  4. customevaporated to about 30 ml
  5. addition30 ml of water and 1.52 g of sodium perborate are then added
  6. distillationis distilled off
  7. customthe precipitate formed
  8. filtrationis filtered off with suction
  9. washwashed with water
  10. customsucked dry
  11. customdried

Sources & evidence

ORD record
ord-fe7d661208c646d79567483dc1848bf3
Source dataset
uspto-grants-2013_10
Patent number
US08563561B2

Reaction notes

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