Isopropylamine → 1,4-dichloro-6-isopropyl-6H-pyrrolo[3,4-d]pyridazine
Reaction equation
Br[CH2:2][C:3]1[C:8]([CH2:9]Br)=[C:7]([Cl:11])[N:6]=[N:5][C:4]=1[Cl:12].C(=O)([O-])[O-].[Na+].[Na+].[CH:19]([NH2:22])([CH3:21])[CH3:20].CCCCCCC>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:11][C:7]1[C:8]2=[CH:9][N:22]([CH:19]([CH3:21])[CH3:20])[CH:2]=[C:3]2[C:4]([Cl:12])=[N:5][N:6]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of 4,5-bis(bromomethyl)-3,6-dichloropyridazine (700 mg, 2.09 mmol) in 66 mL anhydrous THF was added with sodium carbonate (443 mg, 4.18 mmol) and tetrabutylammonium iodide (77.2 mg, 0.21 mmol). The reaction mixture was added with isopropyl amine (0.18 mL, 2.09 mmol) in 10 mL THF dropwisely for 2 h. The reaction mixture was heated at 70° C. for 3 h. The reaction mixture was concentrated, dissolved in DCM and washed with water and brine. The organics solution was dried over Na2SO4 and concentrated to afford a crude oil. The mixture was purified by flash chromatography on silica gel, eluting with 10-80% EtOAc:heptane to afford a off-white solid (280 mg, yield: 47%).
Workup
- concentrationThe reaction mixture was concentrated
- dissolutiondissolved in DCM
- washwashed with water and brine
- dry with materialThe organics solution was dried over Na2SO4
- concentrationconcentrated
- customto afford a crude oil
- customThe mixture was purified by flash chromatography on silica gel
- washeluting with 10-80% EtOAc
Sources & evidence
- ORD record
- ord-9441bd98ad47423c9bcb6f925b4f2f6c
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536168B2
Reaction notes
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