Sodium Iodide → (S)-4-(2-Chloro-6-(iodomethyl)pyrimidin-4-YL)-3-methylmorpholine

HRID 2353708Notes

Reaction equation

HRID 2353708 reaction equation
[I-:1].[Na+].[Cl:3][C:4]1[N:9]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C@@H:11]2[CH3:16])[CH:7]=[C:6]([CH2:17]OS(C)(=O)=O)[N:5]=1>C(Cl)Cl>[Cl:3][C:4]1[N:5]=[C:6]([CH2:17][I:1])[CH:7]=[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][C@@H:11]2[CH3:16])[N:9]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 593799762-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonyloxymethyl)pyrimidine

Product 1

HCID 59380103(S)-4-(2-Chloro-6-(iodomethyl)pyrimidin-4-YL)-3-methylmorpholineYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

Sodium iodide (1.006 ml, 24.61 mmol) was added to 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(methylsulfonyloxymethyl)pyrimidine (1.584 g, 4.92 mmol) in DCM at RT. The resulting solution was refluxed at 40° C. for 18 hours. The reaction mixture was diluted with DCM and washed with water. The organic layer was dried (MgSO4), filtered and evaporated to afford the desired product (1.596 g).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-0e4f3feb1fa84b7eb8d1ccc07623834a
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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