Cyclobutylamine → 5-Chloro-N3-cyclobutylpyridazine-3,4-diamine

HRID 1846058Notes

Reaction equation

HRID 1846058 reaction equation
Cl[C:2]1[N:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[NH2:8].[CH:10]1([NH2:14])[CH2:13][CH2:12][CH2:11]1>O>[Cl:9][C:6]1[C:7]([NH2:8])=[C:2]([NH:14][CH:10]2[CH2:13][CH2:12][CH2:11]2)[N:3]=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 75645CyclobutylamineHCID 64032013,5-Dichloro-1,4-dihydropyridazin-4-imine

Product 1

HCID 867232805-Chloro-N3-cyclobutylpyridazine-3,4-diamineYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 3,5-dichloro-4-aminopyridazine (Preparation 4, 200 mg, 1.22 mmol), cyclobutyl amine (0.56 mL) and water (1.12 mL) was heated under microwave irradiation at 125° C. for 4 hours. The reaction mixture was concentrated in vacuo and the crude residue was purified by silica gel column chromatography eluting with CH2Cl2:MeOH 98:2 to afford the title compound as a brown solid in 58% yield, 140 mg.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude residue was purified by silica gel column chromatography
  3. washeluting with CH2Cl2:MeOH 98:2

Sources & evidence

ORD record
ord-add5d5756e6c4df0b56c1d7bd87cdebc
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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