Methyl morpholine oxide → 4-(2,3-Dihydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[N:8](CC=C)[C:7]=2[N:16]=1.C[N+]1([O-])CC[O:21]CC1.O1CCCC1.O.[CH3:31][C:32]([CH3:34])=[O:33]>C(Cl)(Cl)Cl.[Os](=O)(=O)(=O)=O>[OH:33][CH:32]([CH2:34][OH:21])[CH2:31][N:8]1[C:9](=[O:12])[CH:10]=[N:11][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[N:16][C:7]1=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
In a mixed solvent (25 ml) of tetrahydrofuran/water/acetone (2:1:2) was dissolved 6-methoxy-4-(2-propen-1-yl)pyrido[2,3-b]pyrazin-3(4H)-one (1.20 g, 5.54 mmol), to the solution N-methylmorpholineoxide (1.50 g, 11.08 mmol) was added under cooling on ice and subsequently a 4% aqueous solution of osmium tetroxide (0.70 ml, 0.11 mmol) was added thereto. The reaction solution was stirred for 24 hours while the temperature was raised to room temperature. The reaction solution was diluted with chloroform and washed with saturated sodium bicarbonate water and saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure to yield 1.34 g (96%) of the title compound in the form of a grayish brown solid.
Workup
- temperatureunder cooling on ice
- washwashed with saturated sodium bicarbonate water and saturated sodium chloride solution
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-96a00059e36a4b3ea245f76dd0f9fb6b
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952010B2
Reaction notes
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