Tetrahydrofuran → HCID 66775067, compound

HRID 1645228Notes

Reaction equation

HRID 1645228 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.CS([C:18]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][N:25]=2)[N:21]2[N:34]=[CH:35][N:36]=[C:20]2[N:19]=1)(=O)=O>O>[C:1]1([C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][N:25]=3)[N:21]3[N:34]=[CH:35][N:36]=[C:20]3[N:19]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 25007188HCID 25007188, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 66775067HCID 66775067, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

0.2 mL of a phenyl magnesium bromide 3.0 M tetrahydrofuran solution was added at 0° C. to a tetrahydrofuran (dehydrated) 3 mL solution of 200 mg of 5-(methylsulfonyl)-7-(5-(trifluoromethyl)pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyrimidine, followed by stirring at 0° C. for 5 minutes. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1) to obtain 93 mg of the desired product.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-778ccd8a6189424b8ea7417eb5655df9
Source dataset
uspto-grants-2012_02
Patent number
US08124760B2

Reaction notes

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