Tert-butyl 2,6-dichloro-3-(methylamino)pyridin-4-ylcarbamate → 2,6-dichloro-N3-methylpyridine-3,4-diamine

HRID 2209015Notes

Reaction equation

HRID 2209015 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][CH3:9])=[C:6]([NH:10]C(=O)OC(C)(C)C)[CH:5]=[C:4]([Cl:18])[N:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:7]([NH:8][CH3:9])=[C:6]([NH2:10])[CH:5]=[C:4]([Cl:18])[N:3]=1

Participants

3

Reactant 1

HCID 117843103Tert-butyl 2,6-dichloro-3-(methylamino)pyridin-4-ylcarbamate

Product 1

HCID 889135462,6-dichloro-N3-methylpyridine-3,4-diamine

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl 2,6-dichloro-3-(methylamino)pyridin-4-ylcarbamate 2.44 (0.60 g) was dissolved in a mixture of DCM/TFA 1:1 (5 mL) and stirred at room temperature. After 1 h, LC/MS indicated full conversion to desired product. Mixture was concentrated under reduced pressure, taken up in ethyl acetate, washed with 1N HCl and layers separated. Aqueous layer was extracted again with ethyl acetate and saturated NaHCO3 (aq), and layers separated. Organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to yield 2,6-dichloro-N3-methylpyridine-3,4-diamine 2.45 that was used for next step without further purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C6H7C12N3: 192.0; found: 192.1.

Sources & evidence

ORD record
ord-27e3028cbebe42e089f049ddde9c1c44
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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