Sodium Iodide → (s)-4,6-Diiodo-n-(1-methoxypropan-2-yl)pyrimidin-2-amine

HRID 2056717Notes

Reaction equation

HRID 2056717 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][C@@H:10]([CH3:14])[CH2:11][O:12][CH3:13])[N:3]=1.[IH:15].[I-:16].[Na+].C(Cl)Cl>CCOC(C)=O>[I:15][C:2]1[CH:7]=[C:6]([I:16])[N:5]=[C:4]([NH:9][C@@H:10]([CH3:14])[CH2:11][O:12][CH3:13])[N:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6344DichloromethaneHCID 24841Hydrogen iodideHCID 58612018(s)-4,6-Dichloro-n-(1-methoxypropan-2-yl)pyrimidin-2-amine

Product 1

HCID 58612049(s)-4,6-Diiodo-n-(1-methoxypropan-2-yl)pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (S)-4,6-dichloro-N-(1-methoxypropan-2-yl)pyrimidin-2-amine (260 mg, 0.11 mmol, Example 122(a)), hydriodic acid (57 wt. % in water, 40.4 μl, 0.165 mmol, Aldrich), sodium iodide (248 mg, 0.165 mmol) and DCM (5 mL) was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc (50 mL), washed with 1N NaOH (2×25 mL) and brine (60 mL), dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (7% EtOAc/hexane) to give the title compound. MS (ESI, pos. ion) m/z: 420 (M+1).

Workup

  1. washwashed with 1N NaOH (2×25 mL) and brine (60 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (7% EtOAc/hexane)

Sources & evidence

ORD record
ord-af99575d338e4b58b4be78405911ee49
Source dataset
uspto-grants-2008_02
Patent number
US07335672B2

Reaction notes

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