Sodium Iodide → N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-dipropylamino-acetamide

HRID 732944Notes

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.[CH2:26]([NH:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28].[I-].[Na+]>CC(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][N:29]([CH2:30][CH2:31][CH3:32])[CH2:26][CH2:27][CH3:28])[N:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

N-[4-Amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-chloro-acetamide (0.31 g, 0.65 mmol), N,N-di-n-propylamine (0.33 g, 3.25 mmol) and sodium iodide (20 mg) were added to 20 mL acetone. The reaction mixture was stirred at 55° C. under nitrogen atmosphere for 22 hours, then cooled and concentrated under reduced pressure. The residue was diluted with water and extracted with methylene chloride. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The resulting oil was purified by flash chromatography (methylene chloride/MeOH 100:1) to give 115 mg (33%) of N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-dipropylamino-acetamide, m.p.=129-131° C., MS (M+H)=542.

Workup

temperaturecooled
concentrationconcentrated under reduced pressure
additionThe residue was diluted with water
extractionextracted with methylene chloride
dry with materialThe combined organic layers were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting oil was purified by flash chromatography (methylene chloride/MeOH 100:1)

Sources & evidence

ORD record: ord-9dc85d27f7774bb094f2ef67779ec51d
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589090B2

Reaction notes

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