Azobisisobutyronitrile → 6-(Bromomethyl)-5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

HRID 227606Notes

Reaction equation

HRID 227606 reaction equation
[CH3:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C1C(=O)N([Br:28])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[Br:28][CH2:1][C:2]1[S:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 116162046-Methyl-5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 590995626-(Bromomethyl)-5-(4-nitrophenyl)thieno[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of Example 1D (500 mg, 1.75 mmol) in benzene (50 mL) was treated with NBS (340 mg, 1.91 mmol) and AIBN (50 mg), stirred at reflux for 3.5 hours, and concentrated. The concentrate was absorbed onto silica gel and purified by flash column chromatography with ethyl acetate to provide 330 mg of a 1.7:1 mixture of the desired product and recovered starting material.

Workup

  1. temperatureat reflux for 3.5 hours
  2. concentrationconcentrated
  3. customThe concentrate was absorbed onto silica gel
  4. custompurified by flash column chromatography with ethyl acetate
  5. customto provide

Sources & evidence

ORD record
ord-c83ecd474b394e848d25bff6ff61dd27
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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