Thionyl Chloride → HCID 22249986, compound

HRID 966040Notes

Reaction equation

HRID 966040 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-0f37ba5d46b4477f8f1bdc08427569ff
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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