HCID 11785664, compound → HCID 11154830, compound

HRID 2185622Notes

Reaction equation

HRID 2185622 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[O:4][CH:5]([CH2:10][CH2:11]Br)[C:6]([O:8][CH3:9])=[O:7].CC(C)([O-])C.[K+]>C1COCC1>[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N:18]2[C:23](=[O:24])[CH:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[N:20]([CH3:29])[C:19]2=[O:30])=[CH:13][C:3]=1[O:4][C:5]1([C:6]([O:8][CH3:9])=[O:7])[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 11785664HCID 11785664, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 11154830HCID 11154830, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into 10 ml of THF was dissolved 0.44 g of the obtained methyl 2-[2-chloro-4-fluoro-5-{3-methyl-2,6-dioxo-4-(tri-fluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl}phenoxy]-4-bromobutanoate and 0.10 g of potassium t-butoxide was added to the solution at −15° C. Cooling bath was removed and the solution was stirred until the solution became room temperature taking 2 hours. The reaction solution was poured into aqueous diluted hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (eluent:hexane/ethyl acetate=4/1) to give 0.26 g of methyl 1-[2-chloro-4-fluoro-5-{3-methyl-2,6-dioxo-4-(trifluoro-methyl)-1,2,3,6-tetrahydropyrimidin-1-yl}phenoxy]cyclo-propanecarboxylate (Compound 1-2).

Workup

  1. additionwas added to the solution at −15° C
  2. temperatureCooling bath
  3. customwas removed
  4. custombecame room temperature
  5. additionThe reaction solution was poured into aqueous diluted hydrochloric acid
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-533cb4d50fca432eaeeb4f1af80c37f7
Source dataset
uspto-grants-2002_06
Patent number
US06403534B1

Reaction notes

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