Toluene → HCID 22660237, compound

HRID 393364Notes

Reaction equation

HRID 393364 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:6][C:5]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[NH:17][C:16]2=O)=[C:4]([F:27])[CH:3]=1.P(Cl)(Cl)([Cl:30])=O.C(N(CC)CC)C.C1(C)C=CC=CC=1>[Cl-].[Na+].O>[Cl:30][C:16]1[N:15]([C:5]2[CH:6]=[C:7]([O:8][C:9]3[N:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[C:2]([Cl:1])=[CH:3][C:4]=2[F:27])[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 86589859HCID 86589859, compound

Product 1

HCID 22660237HCID 22660237, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 3-[4-chloro-2-fluoro-5-(2-pyrimidinyloxy)phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione(2.01 g, 0.005 mol), phosphorus oxychloride (3.83 g, 0.025 mol), triethylamine (2.02 g, 0.02 mol and toluene (7 ml) was heated under reflux for 2 hours. The reaction mixture was poured into brine, and extracted with ethyl acetate. The organic phase was separated, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel(40% ethyl acetate/hexane) to give compound III-2 (1.05 g, yield 49.9%) as a white solid, m.p.132-134.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic phase was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel(40% ethyl acetate/hexane)
  8. customto give compound III-2 (1.05 g, yield 49.9%) as a white solid, m.p.132-134.5° C.

Sources & evidence

ORD record
ord-d8df4718b1da4d3a9f69b953c7d7bfa7
Source dataset
uspto-grants-2004_10
Patent number
US06806367B2

Reaction notes

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