Propargyl bromide → HCID 21270771, compound

HRID 1193894Notes

Reaction equation

HRID 1193894 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]=[C:10]2[O:20][CH3:21])=[C:4]([F:22])[CH:3]=1.[CH2:23](Br)[C:24]#[CH:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([O:8][CH2:25][C:24]#[CH:23])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]=[C:10]2[O:20][CH3:21])=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 21270742HCID 21270742, compound

Product 1

HCID 21270771HCID 21270771, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.0 g of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-methoxy-4-trifluoro methyl-6(1H)-pyrimidinone, 1.06 g of propargyl bromide and 1.64 g of potassium carbonate in 5.0 ml of anhydrous acetone is heated at boiling point for 2.5 hours while stirring. The insoluble constituents are subsequently filtered off under suction and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in 100 ml of ethyl acetate and the solution is extracted three times with 50 ml of water each time. The organic phase is then dried over anhydrous sodium sulphate and evaporated to dryness. The residue is recrystallized from diethyl ether/n-hexane. There is obtained 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-2-methoxy-4-trifluoromethyl-6(1H)-pyrimidinone, m.p. 108°-110° C.

Workup

  1. temperatureis heated
  2. customfor 2.5 hours
  3. filtrationThe insoluble constituents are subsequently filtered off under suction
  4. customthe filtrate is evaporated to dryness under reduced pressure
  5. dissolutionThe residue is dissolved in 100 ml of ethyl acetate
  6. extractionthe solution is extracted three times with 50 ml of water each time
  7. dry with materialThe organic phase is then dried over anhydrous sodium sulphate
  8. customevaporated to dryness
  9. customThe residue is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-9d180bb740804c729e613f78fafa78e5
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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