N,N-DIMETHYL-3-NITROPYRIDIN-2-AMINE synthesis

5synthesis methods

Product Name:N,N-DIMETHYL-3-NITROPYRIDIN-2-AMINE
CAS Number:5028-23-9
Molecular formula:C7H9N3O2
Molecular Weight:167.17

1480-87-1
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$6.00/1g

124-40-3
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5028-23-9
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$58.00/100 mg

Yield: 90%

Reaction Conditions:

with potassium carbonate in tetrahydrofuran;N,N-dimethyl-formamide for 16 h;

Steps:

1 Step 1: Synthesis of N,N-dimethyl-3-nitropyridin-2-amine (10-3) :
A DMF solution (1.0 ml/mmol) of 2-fluoro-3-nitro pyridine (1.0g, 7.0 mmol), dimethylamine in THF (2.0 M solution, 4.2 ml, 8.4 mmol) and K₂CO₃ (1.4g, 10.5 mmol) were heated to 100 °C in a sealed tube for 16 hours. TLC and LCMS of the reaction indicated complete consumption of starting material. The reaction mixture was quenched with water, extracted with ethyl acetate, and the organic layer was dried over Na₂SO₄ and evaporated to get crude material, which was purified using isolera column chromatography to afford N,N-dimethyl-3-nitropyridin-2-amine (1.05g, 6.3 mmol, 90.0% yield) as a yellow- colored solid, LCMS (ES⁺, m/z): 168.2 (M+1).

References:

SUMITOMO DAINIPPON PHARMA ONCOLOGY, INC.;SIDDIQUI-JAIN, Adam;SEENISAMY, Jeyaprakashnarayanan;WARNER, Steven, L.;WHATCOTT, Clifford, J.;BEARSS, David, J. WO2021/3417, 2021, A1 Location in patent:Paragraph 00296; 00303; 00310; 00314; 00320; 00340; 00346