3-Amino-6-chloro-4,5-dimethylpyridazine → HCID 71742687, compound

HRID 1501344Notes

Reaction equation

HRID 1501344 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][O-:12].[Na+]>CO>[CH3:11][O:12][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[C:4]([CH3:9])[C:3]=1[CH3:10]

Participants

4

Reactant 2

HCID 69919433-Amino-6-chloro-4,5-dimethylpyridazineHCID 10942334Sodium Methoxide

Product 1

HCID 71742687HCID 71742687, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-Chloro-4,5-dimethylpyridazin-3-amine (CAS-Nr. 76593-36-7, 500 mg, 3.17 mmol, 1.0 eq) in 14.51 mL of a 25% solution (w/w) of sodium methylate in MeOH was heated for 1 h at 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 (Na2SO4 anh.). Volatile components were removed by the use of a rotary evaporator and the crude mixture was purified via MPLC (Biotage Isolera; 25 g SNAP NH2 cartridge: hexane→hexane/EtOAc 1/1) to give 250 mg (49% yield) of the title compound.

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4 anh.)
  4. customVolatile components were removed by the use of a rotary evaporator
  5. customthe crude mixture was purified via MPLC (Biotage Isolera; 25 g SNAP NH2 cartridge: hexane→hexane/EtOAc 1/1)

Sources & evidence

ORD record
ord-e7bbc7c500d74f3ea9258285f2c94795
Source dataset
uspto-grants-2015_12
Patent number
US09206185B2

Reaction notes

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