Water → HCID 12151219, compound

HRID 2415038Notes

Reaction equation

HRID 2415038 reaction equation
Cl[C:2]([C:4]1[C:5]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[N:6][C:7]([CH3:14])=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])=[CH2:3].N12CCCN=C1CCCCC2.O>CS(C)=O>[C:2]([C:4]1[C:5]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[N:6][C:7]([CH3:14])=[N:8][C:9]=1[C:10]([F:11])([F:13])[F:12])#[CH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12151218HCID 12151218, compound

Product 1

HCID 12151219HCID 12151219, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-(1-Chlorovinyl)-4-imidazol-1-yl-2-methyl-6-trifluoromethyl-pyrimidine (0.20 g) was dissolved in dimethylsulfoxide (2 ml) and 1,8-diazabicyclo-[5,4,0]-undec-7-ene (0.11 g) was added at room temperature with stirring. The mixture was stirred for 2 hr in room temperature and then added water. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed 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) to give 5-Ethynyl-4-imidazol-1-yl-2-methyl-6-trifluoromethylpyrimidine (0.11 g) as colorless crystalline solid, mp 121-122° C.

Workup

  1. stirringThe mixture was stirred for 2 hr in room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed water and brine
  4. dry with materialrespectively and dried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform-THF)

Sources & evidence

ORD record
ord-2a5fec20b86c4cb093f2c9c1b26f992e
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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