Piperazin-2-one → [2-(3-Oxopiperazin-1-yl)pyrimidin-5-yl]boronic acid

HRID 626936Notes

Reaction equation

HRID 626936 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][NH:14][CH2:13][C:12]1=[O:17]>O1CCOCC1>[O:17]=[C:12]1[NH:11][CH2:16][CH2:15][N:14]([C:2]2[N:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][N:3]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 231360Piperazin-2-oneHCID 21747362(2-Chloropyrimidin-5-yl)boronic acid

Product 1

HCID 89923662[2-(3-Oxopiperazin-1-yl)pyrimidin-5-yl]boronic acidYield 50.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

(2-Chloropyrimidin-5-yl)boronic acid (1.0 g, 6.32 mmol) and piperazin-2-one (1.6 g, 16.0 mmol) were suspended in 1,4-dioxane (10 mL) and the mixture was heated at 100° C. under microwave irradiation for 45 minutes. The supernatant liquid was decanted from the suspension and the residue was triturated with methanol and diethyl ether. The resultant solids were filtered off and dried under vacuum to afford the title compound (706 mg, 30%) as a pale pink solid. Method B HPLC-MS: MH+ m/z 223, RT 0.25 minutes.

Workup

  1. customThe supernatant liquid was decanted from the suspension
  2. customthe residue was triturated with methanol and diethyl ether
  3. filtrationThe resultant solids were filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b52fb167cd004ee7938c204d46be5842
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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