Imidazole → HCID 12151213, compound

HRID 2415034Notes

Reaction equation

HRID 2415034 reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[N:5]=[C:4](S(C(C)C)(=O)=O)[N:3]=1.[CH2:19]([OH:22])[C:20]#[CH:21].[H-].[Na+].[NH:25]1[CH:29]=[CH:28][N:27]=[CH:26]1>O1CCCC1.O>[N:25]1([C:2]2[C:7]([I:8])=[C:6]([C:9]([F:10])([F:11])[F:12])[N:5]=[C:4]([O:22][CH2:19][C:20]#[CH:21])[N:3]=2)[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 12151421HCID 12151421, compound

Product 1

HCID 12151213HCID 12151213, compoundYield 26.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-5-iodo-2-isopropylsulfonyl-6-trifluoromethypyrimidine (0.79 g) was dissolved in tetrahydrofuran (5.0 ml) and added propargyl alcohol (0.11 g). The mixture was cooled to ice bath temperature and added sodium hydride (oily 80%, 57 mg). The mixture was stirred at that temperature for 10 minutes, and then added imidazole (0.39 g) at the same temperature. The mixture was stirred at that temperature for 30 minutes, and then it warmed to room temperature. After stirring over night, the mixture was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-THF). The fraction was triturated by hexane to give 4-imidazol-1-yl-5-iodo-2-prop-2-ynyloxy-6-trifluoromethyl-pyrimidine (0.20 g) as colorless crystalline solid, mp 128-129° C.

Workup

  1. temperatureThe mixture was cooled to ice bath temperature
  2. stirringThe mixture was stirred at that temperature for 30 minutes
  3. stirringAfter stirring over night
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water and brine
  6. dry with materialrespectively and dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform-THF)
  9. customThe fraction was triturated by hexane

Sources & evidence

ORD record
ord-0479e8c0601e4919bf9b44027f87dcb6
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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