Chloropyrazine → HCID 44325872, compound

HRID 378229

Reaction equation

HRID 378229 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 44325872HCID 44325872, compound

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%

Sources & evidence

ORD record
ord-a97500dcfe004e03807b7b74d83d48f4
Source dataset
uspto-grants-2000_02
Patent number
US06030966

Linked notes

Loading…