Thionyl Chloride → HCID 22249986, compound

HRID 890217Notes

Reaction equation

HRID 890217 reaction equation
O[CH2:2][CH2:3][C:4]1[C:5]([CH3:24])=[N:6][C:7]2[N:8]([N:11]=[C:12]([CH3:23])[C:13]=2[C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])[C:9]=1[OH:10].S(Cl)(Cl)=O>C1C=CC=CC=1>[C:19]1([CH3:20])[CH:18]=[C:17]([CH3:21])[CH:16]=[C:15]([CH3:22])[C:14]=1[C:13]1[C:12]([CH3:23])=[N:11][N:8]2[C:9]3[O:10][CH2:2][CH2:3][C:4]=3[C:5]([CH3:24])=[N:6][C:7]=12

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178424559HCID 178424559, compound

Product 1

HCID 22249986HCID 22249986, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 6-(2-hydroxyethyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol (500 mg, 1.54 mmol) and thionyl chloride (0.26 mL) in benzene (30 mL) was heated under reflux for two hours. After cooling to room temperature, the resulting crystals were collected by filtration. A suspension of the resulting crystals in 2% sodium carbonate was stirred at room temperature for two hours. The crystals were collected by filtration and purified by silica gel column chromatography (50-70% ethyl acetate/hexane), to give the title compound (310 mg) as pale brown crystals.

Workup

  1. temperatureunder reflux for two hours
  2. filtrationthe resulting crystals were collected by filtration
  3. additionA suspension of the resulting crystals in 2% sodium carbonate
  4. filtrationThe crystals were collected by filtration
  5. custompurified by silica gel column chromatography (50-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-62b23adec0254875b1fcc972ba63f4e7
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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