Cyclopropylamine → 5-Chloro-N3-cyclopropylpyridazine-3,4-diamine

Temperature

120 °C

3,5-Dichloro-4-aminopyridazine (5.12 g, 31.2 mmol) was added to cyclopropylamine (37.0 g, 650 mmol) in a stainless steel sealed container (100 mL capacity), to give a homogenous solution. The mixture was heated for 12 hours at 120° C. The reaction mixture was cooled to room temperature then evaporated in vacuo. The residue was dissolved in EtOAc (150 mL) with sonication and stirring. The EtOAc solution was washed with 10% aqueous potassium carbonate solution (2×200 mL), dried over anhydrous MgSO4, then filtered and evaporated in vacuo. The mixture was redissolved in CH2Cl2 and purified using silica gel column chromatography eluting with CH2Cl2 (100 mL), then EtOAc (150 mL) to give the title compound as a light orange solid in 73% yield, 4.2 g.

1. customto give a homogenous solution
2. temperatureThe reaction mixture was cooled to room temperature
3. customthen evaporated in vacuo
4. dissolutionThe residue was dissolved in EtOAc (150 mL) with sonication
5. washThe EtOAc solution was washed with 10% aqueous potassium carbonate solution (2×200 mL)
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. customevaporated in vacuo
9. dissolutionThe mixture was redissolved in CH2Cl2
10. custompurified
11. washeluting with CH2Cl2 (100 mL)

ORD record

ord-8b8531dc749d43c7b6acc0280e5abe6d

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952008B2