2-Chloropyridin-4-amine → 2-(Methylsulfanyl)pyridin-4-amine

HRID 1512117Notes

Reaction equation

HRID 1512117 reaction equation
[CH3:1][S-:2].[Na+].Cl[C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][N:6]=1>CN1C(=O)CCC1>[CH3:1][S:2][C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 844322-Chloropyridin-4-amineHCID 4378561Sodium methanethiolate

Product 1

HCID 534863022-(Methylsulfanyl)pyridin-4-amineYield 265.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

Sodium thiomethoxide (140 mg, 1.98 mmol) was added to a solution of 2-chloropyridin-4-amine (150 mg, 1.17 mmol) in NMP (0.65 mL) in a pressure vessel. The vessel was sealed and heated in a microwave to 200° C. for 800 sec. Purification by silica flash chromatography eluting with 8% MeOH/DCM afforded 2-(methylthio)pyridin-4-amine (435 mg, 50% yield). LC/MS (m/z): 140.9 (MH+), Rt 0.59 minutes.

Workup

  1. customThe vessel was sealed
  2. customPurification by silica flash chromatography
  3. washeluting with 8% MeOH/DCM

Sources & evidence

ORD record
ord-8ae2d65dcad8423aa5f8280ba02473c5
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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