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

HRID 1876774Notes

Reaction equation

HRID 1876774 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[N:11][CH:12]=[CH:13][N:14]=3)[C:9]2=[O:18])=[N:6][CH:7]=1.[BH4-].[Na+].[OH-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:9]([OH:18])[C:10]3[C:15](=[N:14][CH:13]=[CH:12][N:11]=3)[C:16]2=[O:17])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 64519736-(5-chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

6-(5-Chloropyridin-2-yl)-5,7-dioxo-5,6-dihydropyrrolo-[3,4-b]-pyrazine (100g) was suspended in 900 ml water. The slurry was cooled to 0-5° C. and 100 ml (7.2%) of aqueous sodium borohydride solution stabilized with 0.1 g sodium hydroxide was added in 3 hrs under vigorous stirring. Reaction mixture was stirred at 0-5° C. for 4 to 5 hrs. After completion of reaction solid was filtered and washed with 2×300 ml water. The filtered solid was refluxed in 215 ml dichloromethane for 30 min and cooled to 25-30° C. The solid was filtered, washed with 100 ml dichloromethane and dried at 50-60° C. to obtain 82 g of title compound.

Workup

  1. additionwas added in 3 hrs under vigorous stirring
  2. customReaction mixture
  3. customAfter completion of reaction solid
  4. filtrationwas filtered
  5. washwashed with 2×300 ml water
  6. temperatureThe filtered solid was refluxed in 215 ml dichloromethane for 30 min
  7. temperaturecooled to 25-30° C
  8. filtrationThe solid was filtered
  9. washwashed with 100 ml dichloromethane
  10. customdried at 50-60° C.

Sources & evidence

ORD record
ord-79b62fd05b514b80a74caa439c8ca8ca
Source dataset
uspto-grants-2012_11
Patent number
US08309723B2

Reaction notes

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