3-Amino-4-bromo-6-chloropyridazine → 6-Chloro-4-methylpyridazin-3-amine

HRID 715533Notes

Reaction equation

HRID 715533 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[NH2:9].[CH3:10][Zn]C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[Cl:8][C:6]1[N:5]=[N:4][C:3]([NH2:9])=[C:2]([CH3:10])[CH:7]=1

Participants

5

Reactant 2

HCID 220244193-Amino-4-bromo-6-chloropyridazineHCID 178477796HCID 178477796, compound

Product 1

HCID 123536646-Chloro-4-methylpyridazin-3-amineYield 100.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A 100 mL flask was charged with 4-bromo-6-chloropyridazin-3-amine (1 g, 4.80 mmol), dimethylzinc (9.59 mL, 9.59 mmol), Pd(PPh3)4 (0.277 g, 0.240 mmol) and DMF (10 mL). The reaction mixture was stirred at RT. Then the reaction mixture was quenched with MeOH and concentrated. The crude product was loaded onto a 10 g SCX SPE, and 3 volumes of MeOH followed by 3 volumes of 2N ammonia in MeOH were added. The fractions were combined and concentrated to afford 6-chloro-4-methylpyridazin-3-amine (693 mg, 80% yield).

Workup

  1. customThen the reaction mixture was quenched with MeOH
  2. concentrationconcentrated
  3. additionwere added
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7940148f828a48ffb205f7dbaa5c6526
Source dataset
uspto-grants-2015_11
Patent number
US09187464B2

Reaction notes

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