Benzimidazole → HCID 66970519, compound

HRID 1363152Notes

Reaction equation

HRID 1363152 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][O:12][CH2:11][C@H:10]2[CH3:15])[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[NH:27][CH:26]=1>C(#N)C.CCOC(C)=O>[N:25]1([C:2]2[N:7]=[C:6]([NH:8][C@H:9]3[CH2:14][CH2:13][O:12][CH2:11][C@H:10]3[CH3:15])[C:5]([N+:16]([O-:18])=[O:17])=[CH:4][N:3]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=[CH:26]1

Participants

6

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 86610157HCID 86610157, compound

Product 1

HCID 66970519HCID 66970519, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-N-(cis-3-methyl-tetrahydro-2H-pyran-4-yl)-5-nitropyrimidin-4-amine (115 mg) in acetonitrile (5 mL) was added potassium carbonate (300 mg) and benzimidazole (150 mg). The mixture was stirred at 70° C. for 2.5 hours. After diluting with 70 mL EtOAc, the mixture was washed with brine, dried over sodium sulfate, and concentrated in vacuo. Column chromatography (50→100% EtOAc/hexanes) provided 99 mg of the title compound.

Workup

  1. washthe mixture was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-15bfd1b4571a487095a7a5a48eb2fc0f
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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