Hydrochloric Acid → HCID 20130578, compound

HRID 845959Notes

Reaction equation

HRID 845959 reaction equation
N[C:2]1[N:7]([C:8]2[C:9]([F:21])=[CH:10][C:11]([Cl:20])=[C:12]([CH:19]=2)[C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14])[C:6](=[O:22])[N:5]=[CH:4][C:3]=1[C:23]#[N:24].Cl.C([OH:29])(C)C>>[Cl:20][C:11]1[CH:10]=[C:9]([F:21])[C:8]([N:7]2[C:2](=[O:29])[C:3]([C:23]#[N:24])=[CH:4][NH:5][C:6]2=[O:22])=[CH:19][C:12]=1[C:13]([O:15][CH:16]([CH3:18])[CH3:17])=[O:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 20130605HCID 20130605, compound

Product 1

HCID 20130578HCID 20130578, compound

Procedure

3.40 g of isopropyl 5-[6-amino-5-cyano-2-oxo-1(2H)-pyrimidinyl]-2-chloro-4-fluorobenzoate in a solution of 100 ml isopropanol and 10 ml of 2N hydrochloric acid are stirred for 1 hour at room temperature. The reaction mixture is substantially concentrated under reduced pressure and extracted with ethyl acetate. The organic phase is washed with aqueous sodium bicarbonate solution, thereafter with water, and dried over anhydrous sodium sulphate. Then the organic phase is evaporated to dryness under reduced pressure and the residue dissolved in diethyl ether and the solution treated with charcoal and evaporated to dryness. The residue is recrystallized from diethyl ether/n-hexane. Isopropyl 2-chloro-4-fluoro-5-[5-cyano-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, m.p. 143°-145° C., is obtained.

Workup

  1. concentrationThe reaction mixture is substantially concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with aqueous sodium bicarbonate solution
  4. dry with materialwith water, and dried over anhydrous sodium sulphate
  5. customThen the organic phase is evaporated to dryness under reduced pressure
  6. dissolutionthe residue dissolved in diethyl ether
  7. additionthe solution treated with charcoal
  8. customevaporated to dryness
  9. customThe residue is recrystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-599982d025134c81b7cfed0ba94fcbb2
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

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