Allyl bromide → HCID 86642307, compound

HRID 905992Notes

Reaction equation

HRID 905992 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:20](Br)[CH:21]=[CH2:22]>C1COCC1>[CH2:22]([NH:9][C:3]1[C:2]([Br:1])=[N:7][C:6]([Br:8])=[CH:5][N:4]=1)[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 6200042-Amino-3,5-dibromopyrazineHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 86642307HCID 86642307, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,5-dibromo-pyrazin-2-ylamine (5.06 g, 20.00 mmol) in 100 mL of THF was added a solution of LiHMDS in THF (1M, 24 mL) at RT. The reaction mixture was stirred at RT for 2 hr, then allyl bromide (3.5 mL, 40 mmol) was added. The reaction mixture was stirred at RT overnight and quenched with saturated NH4Cl solution and extracted with EtOAc. The organic layer was washed with H2O and brine, dried (MgSO4) concentrated, and purified by SiO2 chromatography (200 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 3.51 g of allyl-(3,5-dibromo-pyrazin-2-yl)-amine as a yellow oil (60% yield).

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. customquenched with saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by SiO2 chromatography (200 g SiO2, hexanes/EtOAc 0-35% EtOAc)

Sources & evidence

ORD record
ord-57c1209047764a23885edc78dc228f24
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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