Water → 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

HRID 1722983Notes

Reaction equation

HRID 1722983 reaction equation
F[B-](F)(F)F.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[CH:9][C:8]=1[N+]#N.[OH2:29]>>[Cl:6][C:7]1[C:8]([OH:29])=[CH:9][C:10]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:11]([F:13])[CH:12]=1

Participants

3

Reactant 2

HCID 962WaterHCID 20025903HCID 20025903, compound

Product 1

HCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Procedure

0 23 g of 2-chloro-5-[3,6-dihydro-2,6-dioxo -3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzenediazonium tetrafluoroborate is added to a solution of 75 g of cupric nitrate trihydrate in 50 ml of water. 67 mg of cuprous oxide are added thereto and the reaction mixture is stirred at room temperature for 10 minutes. The mixture is subsequently filtered, the filtrate is extracted with 50 ml of ethyl acetate and the organic phase is washed and evaporated under reduced pressure. The resulting crude product is crystallized from diethyl ether/n-hexane. There is obtained 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6 -trifluoromethyl-2,4(1H,3H)-pyrimidinedione.

Workup

  1. filtrationThe mixture is subsequently filtered
  2. extractionthe filtrate is extracted with 50 ml of ethyl acetate
  3. washthe organic phase is washed
  4. customevaporated under reduced pressure
  5. customThe resulting crude product is crystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-2a45c55e805e4e39a740c0b22a13fd61
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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