Hydrogen Bromide → 8-Chloroimidazo[1,2-a]pyrazine

HRID 2279638Notes

Reaction equation

HRID 2279638 reaction equation
Br.[NH2:2][C:3]1[C:8]([Cl:9])=[N:7][CH:6]=[CH:5][N:4]=1.Br[CH2:11][CH:12](OCC)OCC.C([O-])([O-])=O.[Na+].[Na+]>CO.O>[Cl:9][C:8]1[C:3]2[N:4]([CH:11]=[CH:12][N:2]=2)[CH:5]=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 2762242-Amino-3-chloropyrazine

Product 1

HCID 102612868-Chloroimidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

HBr (48% in H2O) is added to a solution of 2-amino-3-chloropyrazine (1.2 g, 9.26 mmol) and BrCH2CH(OEt)2 (1.6 mL, 10 mmol) in MeOH and H2O (5 mL and 10 mL) at RT. The mixture is stirred for 24 h at RT and then heated to 40° C. for 48 h. The pH is adjusted to 7 with sat. Na2CO3. The mixture is extracted with CH2Cl2. The organic phase is dried over anhydrous Na2SO4. The product is purified by silica gel column chromatography (4% MeOH in CH2Cl2) to give the title compound as an off white solid.

Workup

  1. temperatureheated to 40° C. for 48 h
  2. extractionThe mixture is extracted with CH2Cl2
  3. dry with materialThe organic phase is dried over anhydrous Na2SO4
  4. customThe product is purified by silica gel column chromatography (4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-eeecd07ef75f48dbaa58e1152b392646
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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