Potassium Acetate → HCID 89812885, compound

HRID 717106Notes

Reaction equation

HRID 717106 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[CH2:12][CH2:11]2)=[O:9])=[N:6][CH:7]=1.[B:20]1(B2OC(C)(C)C(C)(C)O2)[O:24]C(C)(C)C(C)(C)[O:21]1.C([O-])(=O)C.[K+]>O1CCOCC1.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]>[CH:17]1([CH2:16][N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:5]3[N:4]=[CH:3][C:2]([B:20]([OH:24])[OH:21])=[CH:7][N:6]=3)=[O:9])[CH2:11][CH2:12]2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 89812826HCID 89812826, compound

Product 1

HCID 89812885HCID 89812885, compoundYield 71.4%

Reagents, catalysts & solvents 2

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

Procedure

(5-Bromo-pyrimidin-2-yl)-(4-cyclopropylmethyl-piperazin-1-yl)-methanone (46 mg, 0.14 mmol), bis(pinacolato)diboron (43 mg, 0.17 mmol), Pd(dppf)Cl2 (12 mg, 0.014 mmol) and potassium acetate (42 mg, 0.42 mmol) in 1,4-dioxane (0.7 mL) were added to a microwave vial and the reaction mixture purged with N2 for 10 min. The reaction mixture was irradiated using a microwave reactor (300 W, 120° C., 20 min). The reaction mixture was passed through a Si-thiol cartridge (2 g) and the column washed with MeOH (4× column volumes). The solvent was removed in vacuo and purified by reverse phase preparative HPLC-MS. The sample was passed through a SCX-2 cartridge (500 mg) and the column washed with MeOH (4× column volumes). The compound was eluted from the column with 0.5M NH3/MeOH to afford 2-(4-cyclopropylmethyl-piperazine-1-carbonyl)-pyrimidine-5-boronic acid as a white solid (29 mg, 70%).

Workup

  1. customthe reaction mixture purged with N2 for 10 min
  2. customThe reaction mixture was irradiated
  3. custom(300 W, 120° C., 20 min)
  4. washthe column washed with MeOH (4× column volumes)
  5. customThe solvent was removed in vacuo
  6. custompurified by reverse phase preparative HPLC-MS
  7. washthe column washed with MeOH (4× column volumes)
  8. washThe compound was eluted from the column with 0.5M NH3/MeOH

Sources & evidence

ORD record
ord-c5b03f48a4ac46d59138d44ef64f354e
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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