Benzimidazole → HCID 22731922, compound

HRID 2083902Notes

Reaction equation

HRID 2083902 reaction equation
[H-].[Na+].[N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][CH:4]=1.[Br:12][C:13]1[C:14](Cl)=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1.C(OCC)(=O)C>CN(C=O)C.O>[Br:12][C:13]1[C:14]([N:3]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[CH:4]2)=[N:15][C:16]([Cl:19])=[N:17][CH:18]=1

Participants

7

Reactant 4

HCID 5798BenzimidazoleHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 22731922HCID 22731922, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% dispersion in oil; 110 mg, 2.75 mmol) was added to a solution of benzimidazole (295 mg, 2.5 mmol) in DMF (6 ml) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then added dropwise to a cold (0° C.) solution of 5-bromo-2,4-dichloropyrimidine (712 mg, 3.14 mmol) in DMF (6 ml). The mixture was stirred for at 0° C. for 2 hours and then ethyl acetate (20 ml) and water (20 ml) were added. The organic phase was separated and dried and volatile material was removed by evaporation. The residue was purified by column chromatography, eluting with 20% ethyl acetate/DCM, to give the product as a white solid (500 mg, 52%). NMR: 7.4 (m, 2H), 7.8 (m, 2H), 8.8 (s, 1H), 9.3 (s, 1H); MS (MH+): 309, 311.

Workup

  1. stirringThe mixture was stirred for at 0° C. for 2 hours
  2. customThe organic phase was separated
  3. customdried
  4. customvolatile material was removed by evaporation
  5. customThe residue was purified by column chromatography
  6. washeluting with 20% ethyl acetate/DCM

Sources & evidence

ORD record
ord-bbb9f9b599e94bc3b7034752dc086bb6
Source dataset
uspto-grants-2004_04
Patent number
US06716831B1

Reaction notes

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