2-Chloropyridin-4-amine → N2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-pyridine-2,4-diamine

HRID 730300Notes

Reaction equation

HRID 730300 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.[O:9]1[C:14]2[CH:15]=[CH:16][C:17]([NH2:19])=[CH:18][C:13]=2[O:12][CH2:11][CH2:10]1>[Cu]I>[O:9]1[C:14]2[CH:15]=[CH:16][C:17]([NH:19][C:4]3[CH:3]=[C:2]([NH2:1])[CH:7]=[CH:6][N:5]=3)=[CH:18][C:13]=2[O:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 844322-Chloropyridin-4-amineHCID 891481,4-Benzodioxan-6-ylamine

Product 1

HCID 57808069N2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-pyridine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
200 °C

Procedure

In a 5-mL vial was added 4-amino-2-chloropyridine (Aldrich Chemical Company) (1.1 g, 8.7 mmol), 1,4-benzodioxane-6-amine (Aldrich Chemical Company) (5.3 g, 35 mmol) and copper (I) iodide (Aldrich Chemical Company) (0.17 g, 0.87 mmol). The content was sonicated at room temperature for 5 min and then heated in the Smith Microwave Synthesizer at 200° C. for 10 min. The residue was purified by flash chromatography (95:5 dichloromethane:2N NH3 in MeOH) to give the title compound as a dark solid. MS (ESI, pos. ion) m/z: 244 (M+1).

Workup

  1. customThe content was sonicated at room temperature for 5 min
  2. customThe residue was purified by flash chromatography (95:5 dichloromethane:2N NH3 in MeOH)

Sources & evidence

ORD record
ord-afff3fa46f9c4226956cb037f5130b7c
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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