Tetrahydrofuran → HCID 22660241, compound

HRID 393367Notes

Reaction equation

HRID 393367 reaction equation
Cl[C:2]1[N:7]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:11]([Cl:21])=[CH:10][C:9]=2[F:22])[C:6](=[O:23])[CH:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[N:3]=1.[CH3:28][C:29](=[N:31][OH:32])[CH3:30].C(=O)([O-])[O-].[K+].[K+].O1CCCC1>[Cl-].[Na+].O>[Cl:21][C:11]1[C:12]([O:14][C:15]2[N:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:13][C:8]([N:7]2[C:6](=[O:23])[CH:5]=[C:4]([C:24]([F:27])([F:26])[F:25])[N:3]=[C:2]2[O:32][N:31]=[C:29]([CH3:30])[CH3:28])=[C:9]([F:22])[CH:10]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 67180Acetone, oximeHCID 22660237HCID 22660237, compound

Product 1

HCID 22660241HCID 22660241, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 2-chloro-3-[4-chloro-2-fluoro-5-(2-pyrimidinyloxy)phenyl]-6-trifluoromethyl-4(3H)-pyrimidinone(1.52 g, 0.0036 mol), acetone oxime(0.26 g, 0.0036 mol), potassium carbonate(0.50 g, 0.0036 mol) and tetrahydrofuran(15 ml) was heated under reflux for 5 hours. The reaction mixture was poured into brine, and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel(50% ethyl acetate/hexane) to give compound II-11 (1.54 g, yield 93.3%) as a white amorphous solid, m.p 70-80° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel(50% ethyl acetate/hexane)
  7. customto give compound II-11 (1.54 g, yield 93.3%) as a white amorphous solid, m.p 70-80° C.

Sources & evidence

ORD record
ord-e2c1ed93b9dd4dfb8c5de2139fd8777d
Source dataset
uspto-grants-2004_10
Patent number
US06806367B2

Reaction notes

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