Water → HCID 135671385, compound

HRID 231514Notes

Reaction equation

HRID 231514 reaction equation
[F: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.O.[OH-].[K+]>FC(F)(F)C(O)=O>[F: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

6

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 14797Potassium HydroxideHCID 135671368HCID 135671368, compound

Product 1

HCID 135671385HCID 135671385, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

To a 5.0 g portion of 7-(3-fluorophenyl)-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (prepared as described in Ex. 23) in 50 ml of trifluoroacetic acid, stirred under nitrogen and heated to 60° C. was added 7.2 ml of triethylsilane. Heating was continued for 4 hours, then the mixture was stirred at room temperature for 16 hours. The mixture was carefully poured into an ice cooled beaker containing 150 ml of water and 40 g of potassium hydroxide. The precipitate formed was collected, washed with water and dried. The solid was dissolved in dichloromethane and filtered through hydrous magnesium silicate. Evaporation of the filtrate gave a white solid. Recrystallization from isopropyl alcohol gave the desired product, mp 146°-148° C.

Workup

  1. temperatureHeating
  2. customThe precipitate formed
  3. customwas collected
  4. washwashed with water
  5. customdried
  6. dissolutionThe solid was dissolved in dichloromethane
  7. filtrationfiltered through hydrous magnesium silicate
  8. customEvaporation of the filtrate
  9. customgave a white solid
  10. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-d4b85ee0273844dcb73ba662e6e3f318
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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