Sodium Iodide → N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-(2,6-dimethyl-morpholin-4-yl)-acetamide

HRID 732946Notes

Reaction equation

HRID 732946 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.[CH3:26][CH:27]1[O:32][CH:31]([CH3:33])[CH2:30][NH:29][CH2:28]1.[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]2[CH2:28][CH:27]([CH3:26])[O:32][CH:31]([CH3:33])[CH2:30]2)[N:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 1108622,6-DimethylmorpholineHCID 57839077HCID 57839077, compound

Product 1

HCID 25007305N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-(2,6-dimethyl-morpholin-4-yl)-acetamideYield 56%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

N-[4-Amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-chloro-acetamide (477 mg, 1 mmol), 2,6-dimethyl morpholine (0.62 mL, 5 mmol) and sodium iodide (25 mg) were added to 20 mL acetone. The reaction mixture was stirred under nitrogen at 55° C. for 18 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 (0%-20% “Magic Base”/methylene chloride) to give 311 mg of N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-2-(2,6-dimethyl-morpholin-4-yl)-acetamide as an amorphous solid, MS (M+H)=556.

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 (0%-20% “Magic Base”/methylene chloride)

Sources & evidence

ORD record
ord-b02d406c52dd4be98ae1d6ed9ad084fd
Source dataset
uspto-grants-2009_09
Patent number
US07589090B2

Reaction notes

Loading…