N-bromobutanimide → 3-bromopyrazolo[1,5-a]pyrimidin-5(4H)-one

HRID 538981Notes

Reaction equation

HRID 538981 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][C:8]([OH:10])=[N:9][C:4]2=[CH:3][CH:2]=1.[Br:11]N1C(=O)CCC1=O>ClCCl.CN(C=O)C>[Br:11][C:3]1[CH:2]=[N:1][N:5]2[CH:6]=[CH:7][C:8]([OH:10])=[N:9][C:4]=12

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 178516350HCID 178516350, compound

Product 1

HCID 1785163493-bromopyrazolo[1,5-a]pyrimidin-5(4H)-oneYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of pyrazolo[1,5-a]pyrimidin-5-ol (Example 1, Step 1, 28.3 g, 210 mmol) and N-bromosuccinimide (37.3 g, 210 mmol) in dichloromethane (200 mL) and DMF (300 mL) was stirred at ambient temperature for 17 hours. The reaction mixture was concentrated and the product was precipitated using Et2O. The solids were collected by filtration and dried to afford 3-bromopyrazolo[1,5-a]pyrimidin-5-ol (40.4 g, 90%). LCMS (APCI−) m/z 211, 213 [M−H]−.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe product was precipitated
  3. filtrationThe solids were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-72ebef4b34124eb589ebbb618bd5e147
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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