6-chloro-1H,2H,3H,4H-pyrido(2,3-b)pyrazin-3-one → 6-Chloropyrido[2,3-b]pyrazin-3(4H)-one

HRID 509650Notes

Reaction equation

HRID 509650 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[N:12]=1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[CH:9][C:8](=[O:11])[NH:7][C:6]=2[N:12]=1

Participants

4

Reactant 1

HCID 866975616-chloro-1H,2H,3H,4H-pyrido(2,3-b)pyrazin-3-one

Product 1

HCID 866975626-Chloropyrido[2,3-b]pyrazin-3(4H)-oneYield 82.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 6-chloro-1,2-dihydropyrido[2,3-b]pyrazin-3(4H)-one (E-26) (3.68 g, 20 mmol, 1.0 eq) in 1,4-dioxane (80 mL), manganese dioxide (19.4 g, 223 mmol, 11.1 eq) was added. The resulting mixture was stirred at reflux for 2 h then cooled to RT, filtered, the cake was washed with ethyl acetate and methanol. The combined filtrates were concentrated in vacuo to afford the desired product 6-chloropyrido[3,2-b]pyrazin-3(4H)-one (E-27) (3 g, 82% yield) as a pale solid. 1H NMR (300 MHz, DMSO-d6) δ: 13.03 (bs, 1H), 8.19 (m, 2H), 7.38 (d, J=8.4 Hz, 1H); ESI-MS m/z: 180.00 [M−H]−.

Workup

  1. additionwas added
  2. temperatureat reflux for 2 h
  3. filtrationfiltered
  4. washthe cake was washed with ethyl acetate and methanol
  5. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-325bddb3c963437aa41335be1ef4de8a
Source dataset
uspto-grants-2015_08
Patent number
US09096590B2

Reaction notes

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