Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → 6(5-chloro pyridyl)-6,7-dihydro-7-ethoxycarbonylmethyl-5H-pyrrolo[3,4-b]pyrazin-5-one

HRID 2232285Notes

Reaction equation

HRID 2232285 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]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[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 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 64519726-(5-Chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo(3,4-b)pyrazin-5-one

Product 1

HCID 198422466(5-chloro pyridyl)-6,7-dihydro-7-ethoxycarbonylmethyl-5H-pyrrolo[3,4-b]pyrazin-5-oneYield 90.4%

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 ethoxycarbonylmethylenetriphenylphosphorane (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 dichloromethane-ethyl 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 dichloromethane-ethyl 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-199d09f69f644a31a95286878c76c73f
Source dataset
uspto-grants-1988_11
Patent number
US04788191

Reaction notes

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