Sodium methanethiolate → 4,5-Dimethyl-6-(methylthio)pyridazin-3-amine

HRID 1501346Notes

Reaction equation

HRID 1501346 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[C:3]=1[CH3:10].[CH3:11][S-:12].[Na+]>C(O)C>[CH3:9][C:4]1[C:3]([CH3:10])=[C:2]([S:12][CH3:11])[N:7]=[N:6][C:5]=1[NH2:8]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 69919433-Amino-6-chloro-4,5-dimethylpyridazine

Product 1

HCID 717426864,5-Dimethyl-6-(methylthio)pyridazin-3-amineYield 42.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Chloro-4,5-dimethylpyridazin-3-amine (CAS-Nr. 76593-36-7, 400 mg, 2.54 mmol, 1.0 eq) and sodium methanethiolate (196 mg, 2.79 mmol, 1.1 eq) in 10.4 mL ethanol were heated for 1 h to 130° C. in a single mode microwave oven. The reaction mixture was partitioned between DCM and water. The organic phase was washed with brine and dried with sodium sulfate. The resulting mixture was filtered through a Whatman filter and the volatile components were removed in vacuo. The crude mixture was purified via MPLC (Biotage Isolera; 50 g SNAP cartridge: DCM/ethanol 95/5→DCM/ethanol 4/1) to give 182 mg (21% yield) of the title compound in 50% purity (UPLC, area-%).

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationThe resulting mixture was filtered through a Whatman
  5. filtrationfilter
  6. customthe volatile components were removed in vacuo
  7. customThe crude mixture was purified via MPLC (Biotage Isolera; 50 g SNAP cartridge: DCM/ethanol 95/5→DCM/ethanol 4/1)

Sources & evidence

ORD record
ord-6a9d5310699e40b09e87b81b59e507e5
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

Loading…