2-Amino-4-methylpyridine → HCID 58935563, compound

HRID 2401296Notes

Reaction equation

HRID 2401296 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[C:6]=2[N:7]=1.[NH2:21][C:22]1[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=1>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[CH:24][N:23]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([C:16]([O:18][CH3:19])=[O:17])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 58935602HCID 58935602, compound

Product 1

HCID 58935563HCID 58935563, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The dichloro compound of Step 6 (1.98 g, 6.20 mmol) was dissolved in dimethyl sulphoxide (10 mL) and the solution treated with 2-amino-4-methylpyridine (1.34 g, 12.4 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between dichloromethane (300 mL) and water (500 mL) and the dichloromethane layer separated. The organic phase was washed with water (3×100 mL), dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 100:0 to 98:2. The crude product was triturated with ether (50 mL), filtered and concentrated in vacuo to yield the title product, 1.2 g.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (300 mL) and water (500 mL)
  2. customthe dichloromethane layer separated
  3. washThe organic phase was washed with water (3×100 mL)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 100:0 to 98:2
  7. customThe crude product was triturated with ether (50 mL)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4301b274dc043dfb36cd7ef1dff88ef
Source dataset
uspto-grants-2014_08
Patent number
US08796287B2

Reaction notes

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