Benzimidazole → HCID 57612659, compound

HRID 2074181Notes

Reaction equation

HRID 2074181 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:30]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[NH:32][CH:31]=1>C1COCC1.C(OCC)(=O)C>[N:30]1([C:2]2[N:7]=[C:6]([NH:8][CH:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)[C:5]([N+:15]([O-:17])=[O:16])=[C:4]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:3]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[N:32]=[CH:31]1

Participants

6

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 59799573HCID 59799573, compound

Product 1

HCID 57612659HCID 57612659, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To 100 mg (0.3 mmol) of 2-chloro-5-nitro-6-phenyl-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine in 5 mL of THF was added potassium carbonate (213 mg, 1.54 mmol, 5.1 equiv.), followed by benzimidazole (106 mg, 0.9 mmol, 3 equiv.) and the reaction mixture was stirred at 70° C. After 2.5 h, heating was discontinued; the reaction mixture was diluted with 70 mL of ethyl acetate, was washed with water and dried (anhydrous MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (silica gel, elution with 4/1 hexanes/ethyl acetate) to give the desired product (48 mg, 38% yield). LC-MS: tR=7.35 min, MS (EI) m/z 417.2 (MH)+.

Workup

  1. temperatureheating
  2. washwas washed with water
  3. dry with materialdried (anhydrous MgSO4)
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by column chromatography (silica gel, elution with 4/1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ac5ef7a89b9b46ad91a08c7438064a70
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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