Cl[C:2]1[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[NH2:15].C(O)(=O)C>O1CCOCC1.ClCCl>[Br:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[N:7]=[C:6]([CH:8]([OH:10])[CH3:9])[CH:5]=[CH:4][N:3]=2)[CH:16]=[C:17]([CH3:19])[CH:18]=11-(2-Chloropyrimidin-4-yl)ethanol (5.25 g, 33.1 mmol) and 3-bromo-5-methylaniline (9.24 g, 49.7 mmol) were suspended in 1,4-dioxane (30 mL). Acetic acid (1.90 ml, 33.1 mmol) was added, and the resultant mixture was heated to 100° C. for 14 h. The reaction mixture was allowed to cool to room temperature and then was diluted with dichloromethane. The resultant solution was adsorbed on silica gel and purified by column chromatography on silica (10-100% ethyl acetate/hexanes) to afford 1-(2-((3-bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanol as a black semi-solid. MS ESI calc'd. for C13H15BrN3O [M+H]+ 308, 310. found 308, 310.
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