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

HRID 732944
Notes
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Reaction equation

HRID 732944 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8902DipropylamineHCID 57839077N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-chloro-acetamide

Product 1

HCID 24884544N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-dipropylamino-acetamideYield 33%

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

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

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes