Diisopropylethylamine → 6-Chloro-3-nitro-N-(tetrahydro-2H-thiopyran-4-yl)pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

2,6-Dichloro-3-nitropyridine (0.500 g, 2.59 mmol), tetrahydro-2H-thiopyran-4-amine (0.304 g, 2.59 mmol) and DIEA (0.91 mL, 5.19 mmol) were taken up in ethanol (2.0 mL) and heated to 80° C. for 18 h in a sealed tube. The reaction solution was chilled to form a precipitate. The precipitate was collected by vacuum filtration to give the title compound (0.360 g) LCMS m/z=274.1 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 1.70-1.85 (m, 2H), 2.20-2.35 (m, 2H), 2.60-2.90 (m, 4H), 3.90-4.10 (m, 1H), 5.84 (d, J=10.0 Hz, 1H), 8.24 (d, J=9.3 Hz, 1H).

Provenance & Evidence