Azobisisobutyronitrile → 2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine

HRID 32542Notes

Reaction equation

HRID 32542 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13]([S:16][CH3:17])[C:14]=3[N:15]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=[CH:3]1.[Br:24]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:24][C:3]1[N:2]([CH3:1])[C:6]([C:7]2[S:8][C:9]3[N:10]=[CH:11][N:12]=[C:13]([S:16][CH3:17])[C:14]=3[N:15]=2)=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:4]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 691944652-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidine2×

Product 1

HCID 691944812-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo[5,4-d]pyrimidineYield 39%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(1-methyl-4-phenyl-1H-imidazol-5-yl)-7-(methylthio)[1,3]thiazolo-[5,4-d]pyrimidine (Intermediate 42) (0.25 g), N-bromosuccinimide (0.26 g) and AIBN (37 mg) in carbon tetrachloride (30 mL) was heated at 70° C. for 18 hours The suspension was filtered and the residue washed well with CCl4. The solvent was evaporated in vacuo to give a yellow solid. Purification by flash chromatography on silica eluting with EtOAC:hexane (1:9) gave the title compound as a white solid (0.12 g, 39%);

Workup

  1. filtrationwas filtered
  2. washthe residue washed well with CCl4
  3. customThe solvent was evaporated in vacuo
  4. customto give a yellow solid
  5. customPurification by flash chromatography on silica eluting with EtOAC

Sources & evidence

ORD record
ord-40c12e99f5124d6abda2d968f5823005
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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