6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo(3,4-b)pyrazin-5-one → HCID 19842246, compound

HRID 280541

Reaction equation

HRID 280541 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16](=O)[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[CH:9]2[OH:18])=[N:6][CH:7]=1.[CH2:19]([O:21][C:22]([CH:24]=[PH3])=[O:23])[CH3:20]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[N:14][CH:13]=[CH:12][N:11]=3)[CH:16]2[CH2:24][C:22]([O:21][CH2:19][CH3:20])=[O:23])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 64519726-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo(3,4-b)pyrazin-5-oneHCID 178473136HCID 178473136, compound

Product 1

HCID 19842246HCID 19842246, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one (1.05 g) and ethoxycarbonylmethylenephosphorane (1.39 g) were dissolved in dry toluene (30 ml) and the solution was refluxed for 6 hours. After cooling, the solvent was distilled off and the residue was purified by silica gel column chromatography. Fractions eluted with dichloromethaneethyl acetate (2:1) were collected and the solvent was distilled off to give crude crystals. Recrystallization from ether-dichloromethane (5:1) gave 1.2 g of 6(5-chloro pyridyl)-6,7-dihydro-7-ethoxycarbonylmethyl-5H-pyrrolo[3,4-b]pyrazin-5-one

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography
  5. washFractions eluted with dichloromethaneethyl acetate (2:1)
  6. customwere collected
  7. distillationthe solvent was distilled off
  8. customto give crude crystals
  9. customRecrystallization from ether-dichloromethane (5:1)

Sources & evidence

ORD record
ord-ba86b2d0b78c45319c2a349e57e30aad
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Linked notes

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