Sodium hydride → HCID 86616961, compound

HRID 1865879Notes

Reaction equation

HRID 1865879 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Cl>CN(C)C=O>[Br:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[C:5]([N:8]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 960701-Bromo-5-chloropentaneHCID 86616962HCID 86616962, compound

Product 1

HCID 86616961HCID 86616961, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.5 g (0.0018 mol) 5-bromo-3-(4-chloro-phenyl)-pyrazin-2-ylamine in 10 ml dimethylformamide was added at room temperature 0.240 g sodium hydride 55% in oil (0.006 mol) and 0.49 g 1-bromo-5-chloro-pentane (0.0025 mol) and the mixture was stirred at room temperature for 0.5 hours. Another 0.130 g sodium hydride 55% in oil was added and the mixture was stirred at room temperature for 2.5 h. The resulting mixture was partitioned between 10% aqueous citric acid and ethyl acetate. The phases were separated, the organic phase was dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel using a gradient of 30% ethyl acetate in heptane to ethyl acetate to yield 0.043 g (83% yield) of the title compound as slightly brownish oil. MS (ISP) (M+H+)=354.1 and 356.0.

Workup

  1. stirringthe mixture was stirred at room temperature for 2.5 h
  2. customThe resulting mixture was partitioned between 10% aqueous citric acid and ethyl acetate
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel using a gradient of 30% ethyl acetate in heptane to ethyl acetate

Sources & evidence

ORD record
ord-c00a429616be4122bfd83738f42abeed
Source dataset
uspto-grants-2009_12
Patent number
US07629346B2

Reaction notes

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