4-Pyridinamine,2,5-dichloro-(9CI)
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4-Pyridinamine,2,5-dichloro-(9CI)
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CAS No:
405230-82-2
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Formula:
C5H4Cl2N2
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Chemical Name:
4-Pyridinamine,2,5-dichloro-(9CI)
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Synonyms:
4-Pyridinamine,2,5-dichloro-(9CI);4-Amino-2,5-dichloropyridine;2,5-dichloropyridin-4-amine;4-PyridinaMine,2,5-dichloro-;5-dichloropyridin-4-aMine;2,5-Dichloro-4-pyridinaMine;2,5-Dichloro-4-aMinopyridine;2,5-Dichloro-pyridin-4-ylaMine
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CAS No:
4-Pyridinamine,2,5-dichloro-(9CI) Use and Manufacturing
A stirred solution of compound 1 (3g, 18.51 mmol, 1 eq), andcompound 2 (4.2ml, 22.22mmol, 1.2eq) in Dry DMF (30ml) was degassed withargon for 20 min followed by the addition of Pd (PPh3)4 (370mg, 0.320mmol, 0.025eq) and Cs2C03 (1.2 eq) at RT then heated to gooc in a sealed tube for16h. Then, the reaction mixture was cooled to RT and quenched with ice-water(300ml) and diluted with EtOAc (200ml), which was filtered through a celitebed; celite bed was washed with EtOAc (2x20ml). The combined organic layerwas dried over Na2S04 and concentrated under reduced pressure to give acrude product. The crude compound was purified by column chromatography(silica gel 100-200 mesh) using 10%% EtOAc in petroleum ether as an eluentto give 5-chloro-2-(prop-1-en-2-yl)pyridin-4-amine (1.7g, 54.83%) as an offwhite solid. LCMS: m/z 169.0% (M+H):General procedure: A microwave vial charged with A solution of (2S, 6R)-2, 6-dimethylpiperazine (2 g, 12.36 mmol, 1 .0 eq), and A solution of To a solution of tert-butyl (2, 5-dichloropyridin-4- yl)carbamate (10 g, 38.17 mmol, 1 eq) in DCM (100 mL) was added trifluoroacetic acid (34 mL, 12 eq) in a dropwise manner at 0C and the mixture allowed to warm to RT and stir for 16 h. TLC analysis indicated formation of a polar spot. Then, the reaction mixture was concentrated under reduced pressure to give the TFA salt of the desired product, which was dissolved in water (50 mL), basified with saturated NaHC03 and extracted in EtOAc (3x50 mL). The combined organic layer was dried over Na2S04 and concentrated under reduced pressure to give crude product. The crude compound was purified by washing with n-pentane to give analytically pure 2, 5-dichloropyridin- 4-amine (6 g, 97%) as an off-white solid. LC-MS m/z 163.14 (M + H).
Computed Properties
Molecular Weight:163.00
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:161.9751535
Monoisotopic Mass:161.9751535
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:99
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-Pyridinamine,2,5-dichloro-(9CI)
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