Azobisisobutyronitrile → 2-Bromomethyl-4,6-bis-(4-methoxy-phenyl)-pyrimidine

HRID 19506Notes

Reaction equation

HRID 19506 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[N:12]=[C:11]([CH3:23])[N:10]=2)=[CH:5][CH:4]=1.[Br:24]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:24][CH2:23][C:11]1[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:12]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 445413204,6-Bis-(4-methoxy-phenyl)-2-methyl-pyrimidine

Product 1

HCID 590076462-Bromomethyl-4,6-bis-(4-methoxy-phenyl)-pyrimidine

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

4,6-Bis-(4-methoxy-phenyl)-2-methyl-pyrimidine 23 (0.21 g, 0.7 mmol) is dissolved in 4 mL carbon tetrachloride. N-Bromo-succinimide (0.10 g, 0.56 mmol) is added and the mixture is heated to 75° C. with stirring. Solid 2,2′-azobisisobutyronitrile (AIBN) (0.01 g, 0.06 mmol) is added and the mixture is stirred at 75° C. for 24 hours. Cooling, diluting with dichloromethane, washing with water, saturated aqueous NaHCO3, and brine, followed by drying over solid Na2SO4 and concentration yielded 2-bromomethyl-4,6-bis-(4-methoxy-phenyl)-pyrimidine 24 as an oil. It is used without further purification in the next step. 1H-NMR (400 MHz, CDCl3) δ=8.02 (d, J=8.8 Hz, 2H), 7.69 (s, 1H), 6.94 (d, J=8.8 Hz, 2H), 3.82 (s, 2H).

Workup

  1. stirringthe mixture is stirred at 75° C. for 24 hours
  2. temperatureCooling
  3. washwashing with water, saturated aqueous NaHCO3, and brine
  4. dry with materialby drying over solid Na2SO4 and concentration

Sources & evidence

ORD record
ord-17fcc6621e5844adbf2d8721b7e065b6
Source dataset
uspto-grants-2010_06
Patent number
US07745445B2

Reaction notes

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