Chloropyrazine → (S)-2-(1-methyl-2-pyrrolidinylmethoxy)pyrazine

HRID 1420520Notes

Reaction equation

HRID 1420520 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].CC(C)([O-])C.[K+].Cl[C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1>C1COCC1>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 73277ChloropyrazineHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 44325872(S)-2-(1-methyl-2-pyrrolidinylmethoxy)pyrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-1-methyl-2-pyrrolidinemethanol (1.15 g) in THF (45 mL) was treated with potassium tert-butoxide (1.2 g). After 10 min, chloropyrazine was added and the reaction stirred for 1.5 h. The reaction was quenched with 5 N HCl (4 mL) and the solvent evaporated. The residue was suspended in water and extracted with ether. The aqueous fraction was made basic and extracted with CHCl3. The extracts were dried, the solvent evaporated, and the residue purified by radial chromatography eluting with 20%-EtOH-2%-NH4OH-CHCl3 to give (S)-2-(1-methyl-2-pyrrolidinylmethoxy)pyrazine (1.1). The HCl salt crystallized from EtOAc as a white solid, m.p. 121-122° C. (Compound 28)

Workup

  1. customThe reaction was quenched with 5 N HCl (4 mL)
  2. customthe solvent evaporated
  3. extractionextracted with ether
  4. extractionextracted with CHCl3
  5. customThe extracts were dried
  6. customthe solvent evaporated
  7. customthe residue purified by radial chromatography
  8. washeluting with 20%-EtOH-2%-NH4OH-CHCl3

Sources & evidence

ORD record
ord-51486aa179df4d81a5ebefb9c6f90d78
Source dataset
uspto-grants-2000_06
Patent number
US06071900

Reaction notes

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