4-Chloro-3-iodopyridin-2-amine → 4-Chloro-3-(methylthio)pyridin-2-amine

HRID 919300Notes

Reaction equation

HRID 919300 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1I.C(S)[CH2:11][S:12]([O-])(=O)=O.[Na+]>CC(O)C.[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[S:12][CH3:11]

Participants

5

Reactant 2

HCID 229365964-Chloro-3-iodopyridin-2-amineHCID 23662354Mesna

Product 1

HCID 901770754-Chloro-3-(methylthio)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution 4-chloro-3-iodopyridin-2-amine (400 mg, 1.57 mmol), CuI (30 mg, 0.157 mmol) in i-PrOH (3 mL) and glycol (10 mg, 0.157 mmol) was added MeSNa (110 mg, 1.57 mmol). The resulting mixture was allowed to stir at 100° C. for 24 h. The reaction mixture was concentrated and the resulting residue was purified by column chromatography to afford the title compound as oil. LC/MS m/z=175.19 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-8d29595a5d554f4eaeea9f08677180aa
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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