1,4-Dioxane → 5-(4-Chloro-phenyl)-6-cyclobutoxy-pyridin-3-ylamine
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([O:21][CH:22]2[CH2:25][CH2:24][CH2:23]2)=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:13]=1)(C)(C)C.O1CCOCC1>Cl>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:13]=[C:8]([NH2:7])[CH:9]=[N:10][C:11]=2[O:21][CH:22]2[CH2:25][CH2:24][CH2:23]2)=[CH:15][CH:16]=1Participants
4
Procedure
[5-(4-Chloro-phenyl)-6-cyclobutoxy-pyridin-3-yl]-carbamic acid tert-butyl ester (1.042 g, 2.78 mmol) was dissolved in 4M HCl in dioxane (10.4 ml, 41.7 mmol). The reaction mixture was a light yellow solution and was stirred at room temperature for 1 h. The mixture was partitioned between ethyl acetate and 1M Na2CO3 solution. The organic phases were combined, dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, 5% to 75% ethyl acetate in heptane) to give 0.358 g (46.9%) of the title compound as light red oil; LC-MS (UV peak area/ESI) 94.3%, 275.0950 (M+H)+.