Diethyl Ether → HCID 59852417, compound

HRID 2373169Notes

Reaction equation

HRID 2373169 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][N:15]=1.[CH3:17][O:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)C>CN(C)C=O>[CH3:17][O:18][CH2:19][CH2:20][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:16])=[N:12][CH:13]=[CH:14][N:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 103079622-[(3-Amino)-2-pyrazinyl]benzimidazole

Product 1

HCID 59852417HCID 59852417, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1H-benzimidazol-2-yl)pyrazin-2-amine (0.302 g, 0.14 mmol) was dissolved in N,N-dimethyl formamide (10 mL) and treated with 2-bromoethyl methyl ether (0.15 mL, 0.16 mmol) and cesium carbonate (0.475 g, 1.4 mmol). The mixture was stirred at ambient temperature for 20 hours and then filtered through celite. The filtrate was concentrated and partitioned between ethyl acetate and water. The mixture was extracted into ethyl acetate (×3) and the combined organic layers were washed with water, and then with saturated sodium chloride. The organics were dried over magnesium sulfate, filtered and concentrated. Trituration with diethyl ether afforded the title compound as tan solids (0.275 g, 0.10 mmol).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between ethyl acetate and water
  4. extractionThe mixture was extracted into ethyl acetate (×3)
  5. washthe combined organic layers were washed with water
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0a84dc5fb5bf49c995295ccf485f4826
Source dataset
uspto-grants-2008_12
Patent number
US07459454B2

Reaction notes

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