Hydrochloric Acid → HCID 23227016, compound

HRID 1956181Notes

Reaction equation

HRID 1956181 reaction equation
Br[C:2]1[C:3]([S:8][CH3:9])=[N:4][CH:5]=[N:6][CH:7]=1.C([Li])CCC.[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19].Cl>O1CCCC1.CCCCCC>[F:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]([C:2]1[C:3]([S:8][CH3:9])=[N:4][CH:5]=[N:6][CH:7]=1)[OH:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 67970o-FluorobenzaldehydeHCID 122700805-bromo-4-methylthiopyrimidineHCID 178418339Butyllithium

Product 1

HCID 23227016HCID 23227016, compoundYield 39.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-25 °C

Procedure

To a slurry of 20 g (98 mmol) of 5-bromo-4-methylthiopyrimidine in 200 mL of anhydrous tetrahydrofuran at -90° C. was slowly added with stirring and cooling 40 mL (100 mmol) of 2.5M n-butyl lithium in hexane. After a 20-min reaction period, 13.3 g of 2-fluorobenzaldehyde was added with stirring. The solution was allowed to gradually warm to -25° C. It was then poured into dilute aqueous hydrochloric acid with stirring. The resulting mixture was extracted with ether and the ethereal extract was dried over magnesium sulfate, filtered, and partially concentrated by evaporation under reduced pressure. The remaining mixture was diluted with hexane and the solids that formed were collected by filtration to obtain 9.75 g of the title compound as colorless solid melting at 176°-177° C.

Workup

  1. additionwas added
  2. stirringwith stirring
  3. stirringwith stirring
  4. extractionThe resulting mixture was extracted with ether
  5. extractionthe ethereal extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationpartially concentrated by evaporation under reduced pressure
  9. additionThe remaining mixture was diluted with hexane
  10. customthe solids that formed
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8302036683e04948b20b71b12a21a56e
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

Loading…