2-Amino-3-methylpyrazine → 2-Cyclopropyl-8-methylimidazo[1,2-a]pyrazine

HRID 869600Notes

Reaction equation

HRID 869600 reaction equation
[CH3:1][C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=1.Br[CH2:10][C:11]([CH:13]1[CH2:15][CH2:14]1)=O.C(=O)([O-])O.[Na+]>COCCOC.C1COCC1>[CH:13]1([C:11]2[N:8]=[C:3]3[C:2]([CH3:1])=[N:7][CH:6]=[CH:5][N:4]3[CH:10]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 3

HCID 3022842-Amino-3-methylpyrazineHCID 516892Sodium BicarbonateHCID 109208412-Bromo-1-cyclopropylethan-1-one

Product 1

HCID 867214522-Cyclopropyl-8-methylimidazo[1,2-a]pyrazineYield 43%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

[step 1] 3-Methylpyrazin-2-amine (16 g, 147 mmol) was dissolved in 1,2-dimethoxyethane (122 mL) and THF (61 mL), 2-bromo-1-cyclopropylethanone (36 g, 220 mmol) was added, and the mixture was stirred at room temperature for 70 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the mixture, and the mixture was extracted 3 times with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-85/15 v/v) to give 2-cyclopropyl-8-methylimidazo[1,2-a]pyrazine (11g, 43%).

Workup

  1. extractionthe mixture was extracted 3 times with chloroform
  2. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 v/v-85/15 v/v)

Sources & evidence

ORD record
ord-4e043acd524d49a8b1e0e2c908309b0c
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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