Triethylsilane → HCID 135671382, compound

HRID 231515Notes

Reaction equation

HRID 231515 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]3[N:14]=[CH:15][C:16]([C:17]#[N:18])=[C:12]3[NH:11][CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.[OH-].[K+]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:13]3[N:14]=[CH:15][C:16]([C:17]#[N:18])=[C:12]3[NH:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 14797Potassium HydroxideHCID 135671375HCID 135671375, compound

Product 1

HCID 135671382HCID 135671382, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
55 °C

Procedure

To an 8.0 g portion of 7-(3-chlorophenyl)-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (prepared as described in Ex. 30) in 65 ml of trifluoroacetic acid, stirred under nitrogen and heated to 55° C. was added 7.3 ml of triethylsilane. The reaction mixture was stirred and heated at 60° C. for 71/2 hours. The mixture was then carefully poured into an ice cooled beaker containing 100 ml of 25% aqueous potassium hydroxide. The precipitate which formed was collected by filtration and dissolved in chloroform. The chloroform solution was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give 6.8 g of white crystals. The crystals were triturated with ether. The ether was collected and crystals formed. The crystals were washed with ether and gave 2.8 g of white crystals. The crude product, 2.8 g, was chromatographed on a liquid chromatograph using a silica gel column and eluting with 5% ethyl acetate/chloroform. The fraction containing the desired product was collected and evaporated in vacuo and gave crystals, mp 148°-150° C.

Workup

  1. temperatureheated at 60° C. for 71/2 hours
  2. customThe precipitate which formed
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in chloroform
  5. washThe chloroform solution was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a6e735edd7b74dc381e118bed61043ba
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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