HCID 58001769, compound → 4-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1943193Notes

Reaction equation

HRID 1943193 reaction equation
[CH3:1][C:2]1([CH3:21])[O:7][CH2:6][CH:5]([N:8]2[C:13](=[O:14])[CH2:12][NH:11][C:10]3[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[N:18][C:9]2=3)[CH2:4][O:3]1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1([CH3:21])[O:3][CH2:4][CH:5]([N:8]2[C:13](=[O:14])[CH:12]=[N:11][C:10]3[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[N:18][C:9]2=3)[CH2:6][O:7]1

Participants

4

Reactant 1

HCID 58001769HCID 58001769, compound

Product 1

HCID 580017664-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 69.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(2,2-Dimethyl-1,3-dioxan-5-yl)-6-(methyloxy)-1,4-dihydropyrido[2,3-b]pyrazin-3(2H)-one (25.37 g) and activated manganese dioxide (120 g, ˜15 eq.) were stirred in DCM (500 ml) at room temperature for 2 hours then overnight. The mixture was filtered with suction and the solids were washed with DCM (2×100 ml). The combined filtrate plus washings were evaporated under reduced pressure to give a brown foam; this was purified by column chromatography on silica (eluting with 0%-100% ethyl acetate in petroleum ether (40-60°)). Appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a light tan solid (17.40 g, 69%).

Workup

  1. customovernight
  2. filtrationThe mixture was filtered with suction
  3. washthe solids were washed with DCM (2×100 ml)
  4. customThe combined filtrate plus washings were evaporated under reduced pressure
  5. customto give a brown foam
  6. customthis was purified by column chromatography on silica (eluting with 0%-100% ethyl acetate in petroleum ether (40-60°))
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d6665989cfa440859d7722b4561b69c4
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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