Methanol → 3-(3-Chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol

HRID 633835Notes

Reaction equation

HRID 633835 reaction equation
C[N+]1([O-])CC[O:5]CC1.[CH2:9]([C:12]1[C:13]([Cl:24])=[CH:14][N:15]=[C:16]2[C:21]=1[N:20]=[C:19]([O:22][CH3:23])[CH:18]=[CH:17]2)[CH:10]=C.[CH3:25][OH:26]>ClCCl.O.O.O.[Os](=O)(=O)=O.[K]>[Cl:24][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[CH2:9][CH:10]([OH:5])[CH2:25][OH:26])=[N:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2

Participants

7

Reactant 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 671828908-Allyl-7-chloro-2-methoxy-[1,5]naphthyridine

Product 1

HCID 671805623-(3-Chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diolYield 96%

Reagents, catalysts & solvents 3

HCID 178526964HCID 178526964, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-Methylmorpholine-N-oxide (0.76 g, 64.0 mmol, 1.5 eq) is added at room temperature to a stirred solution of 8-allyl-7-chloro-2-methoxy-[1,5]naphthyridine (1.0 g, 4.26 mmol, 1.0 eq) in dichloromethane (40 mL) and water (4 mL), followed by potassium osmium(VI) oxide dihydrate (80 mg, 0.23 mmol, 0.05 eq). After 16 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×20 mL) and a saturated sodium sulfite aqueous solution (20 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 40:1, v/v) to afford 3-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol as a light yellow solid (1.1 g, 96% yield).

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-f9131a8b54c74f4980b72c37781675c1
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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