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

HRID 1890284Notes

Reaction equation

HRID 1890284 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[S:12]1[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]1.CCN(C(C)C)C(C)C>C(O)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:18][CH:15]2[CH2:16][CH2:17][S:12][CH2:13][CH2:14]2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 418807Tetrahydrothiopyran-4-ylamine

Product 1

HCID 866552536-Chloro-3-nitro-N-(tetrahydro-2H-thiopyran-4-yl)pyridin-2-amineYield 50.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  1. temperatureThe reaction solution was chilled
  2. customto form a precipitate
  3. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-3b8cfb6d0dde465fbea34d5bc04e946e
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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