Dimethyl Sulfoxide → 4-(2-(5-aminopyridin-2-yloxy)pyridin-3-yl)-N-methylpyridin-2-amine

HRID 2361039Notes

Reaction equation

HRID 2361039 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.CS(C)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:20]1[C:25]([C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH3:33])[CH:27]=2)=[CH:24][CH:23]=[CH:22][N:21]=1>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:20]2[C:25]([C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][CH3:33])[CH:27]=3)=[CH:24][CH:23]=[CH:22][N:21]=2)=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 161089834-(2-chloropyridin-3-yl)-N-methylpyridin-2-amineHCID 178507770HCID 178507770, compound

Product 1

HCID 577562284-(2-(5-aminopyridin-2-yloxy)pyridin-3-yl)-N-methylpyridin-2-amine

Procedure

In a microwave vial, 5-aminopyridin-2-ol (125 mg, 1.14 mmol) was dissolved in DMSO (0.910 mL, 0.228 mmol) and cesium carbonate (445 mg, 1.37 mmol) was added. The vial was capped with a septum and the reaction was stirred at RT for 25 minutes until a paste was formed. Then 4-(2-chloropyridin-3-yl)-N-methylpyridin-2-amine (50 mg, 0.23 mmol) was added and the vial was sealed and heated to 180° C. in Personal Chemistry Microwave for 15 min. The mixture was extracted with EtOAc, organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The product was purified by column chromatography on silica gel using 60:40 DCM:(90:10:1 DCM:MeOH:NH4OH to flush out top spots, then 50:50 DCM:(90:10:1 DCM:MeOH:NH4OH) to collect the product. Green solid, 4-(2-(5-aminopyridin-2-yloxy)pyridin-3-yl)-N-methylpyridin-2-amine was obtained. MS m/z=294 [M+1]+. Calcd for C16H15N5O: 293.13.

Workup

  1. customThe vial was capped with a septum
  2. customwas formed
  3. customthe vial was sealed
  4. temperatureheated to 180° C. in Personal Chemistry Microwave for 15 min
  5. extractionThe mixture was extracted with EtOAc, organic layers
  6. washwere washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by column chromatography on silica gel using 60:40 DCM
  11. custom(90:10:1 DCM:MeOH:NH4OH to flush out top spots
  12. custom50:50 DCM:(90:10:1 DCM:MeOH:NH4OH) to collect the product

Sources & evidence

ORD record
ord-cc437bd7fbb647f9b71a48a424c0cb2f
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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