Acetone → N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-cyclopentylamino-acetamide

Reaction equation

[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([I:15])[C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH:18]([CH3:20])[CH3:19])=[CH:6][N:5]=[C:4]([NH:21][C:22](=[O:25])[CH2:23]Cl)[N:3]=1.[CH:26]1([NH2:29])[CH2:28][CH2:27]1.[I-].[K+].[CH3:32][C:33](C)=O>>[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([I:15])[C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH:18]([CH3:20])[CH3:19])=[CH:6][N:5]=[C:4]([NH:21][C:22](=[O:25])[CH2:23][NH:29][CH:26]2[CH2:33][CH2:32][CH2:27][CH2:28]2)[N:3]=1

Participants

Reactant 4

HCID 180Acetone

HCID 4875Potassium Iodide

HCID 69828Cyclopropylamine

HCID 57839077N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-chloro-acetamide

Product 1

HCID 25007306N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-cyclopentylamino-acetamide

Procedure

N-[4-Amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-chloro-acetamide (1.13 g, 2.37 mmol), cyclopropylamine (0.807 g, 9.48 mmol), and potassium iodide (25 mg) were added to 25 mL acetone. The reaction mixture was stirred under nitrogen at room temperature for 20 hours, then diluted with EtOac. The mixture was washed with water and brine, and the organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (8% MeOH/methylene chloride-0.1% NH4OH) to give 15 mg of N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-cyclopentylamino-acetamide, m.p.=176.5-178.0° C., MS (M+H)=526.