Dicyclohexylcarbodiimide → 3-pentanone O-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoyl}oxime

HRID 2248556

Reaction equation

HRID 2248556 reaction equation
[CH3:1][CH2:2][C:3](=[N:6][OH:7])[CH2:4][CH3:5].[Cl:8][C:9]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:14][C:10]=1[C:11](O)=[O:12].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>C(OCC)C>[Cl:8][C:9]1[CH:17]=[C:16]([F:18])[C:15]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:14][C:10]=1[C:11]([O:7][N:6]=[C:3]([CH2:4][CH3:5])[CH2:2][CH3:1])=[O:12]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 28017453-Pentanone oximeHCID 120567892-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoic acid

Product 1

HCID 199942333-pentanone O-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoyl}oxime

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.9 g of 3-pentanone oxime is added at room temperature to a suspension of 3.0 g of 2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoic acid in 50 ml of diethyl ether. Thereafter, a solution of 1.9 g of dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine in 15 ml of diethyl ether is added dropwise over 10 minutes. The reaction mixture is stirred at room temperature for 12 hours. Subsequently, it is filtered and evaporated to dryness under reduced pressure. The residue is purified by chromatography on silica gel with n-hexane/diethyl ether (4:1) as the eluent. In this manner there is obtained 3-pentanone O-{2-chloro-5-[3,6-dihydro-2,6-dioxo-3-methyl-4 -trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzoyl}oxime, m.p. 128°-130° C.

Workup

  1. filtrationSubsequently, it is filtered
  2. customevaporated to dryness under reduced pressure
  3. customThe residue is purified by chromatography on silica gel with n-hexane/diethyl ether (4:1) as the eluent

Sources & evidence

ORD record
ord-e86122d1c61647a2b918633f26b6c004
Source dataset
uspto-grants-1991_08
Patent number
US05041156

Linked notes

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