Azobisisobutyronitrile → 5-Bromo-2-(bromomethyl)pyrimidine

HRID 1496931Notes

Reaction equation

HRID 1496931 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.[Br:9]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][Br:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 143877445-Bromo-2-methylpyrimidine

Product 1

HCID 205577975-Bromo-2-(bromomethyl)pyrimidineYield 11%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-2-methylpyrimidine (119) (1.34 g, 7.75 mmol), N-bromosuccinimide (1.40 g, 7.87 mmol) and AIBN (0.13 g, 0.79 mmol) in CCl4 (15 mL) was stirred at 60° C. for 3 h. The resulting mixture was filtered, the filter cake was washed with Et2O (100 mL), and the combined filtrates were concentrated under reduced pressure. Column chromatography of the residue, eluting with 2:1 EtOAc:hexanes, gave 5-bromo-2-(bromomethyl)pyrimidine (120) (0.214 g, 11%) as a white solid: mp 55-57° C.; 1H NMR (CDCl3) δ 8.79 (s, 2H), 4.57 (s, 2H). Anal. (C5H4Br2N2) C, H, N.

Workup

  1. filtrationThe resulting mixture was filtered
  2. washthe filter cake was washed with Et2O (100 mL)
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. washColumn chromatography of the residue, eluting with 2:1 EtOAc

Sources & evidence

ORD record
ord-b178772538d1467d96e8c190228d2701
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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