Methanol → HCID 18759300, compound

HRID 433735Notes

Reaction equation

HRID 433735 reaction equation
[F:1][C:2]1[C:3]([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:4][C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)=[C:6]([C:8]#[N:9])[CH:7]=1.CO>C(Cl)(Cl)Cl.B(Br)(Br)Br>[C:8]([C:6]1[CH:7]=[C:2]([F:1])[C:3]([N:19]2[C:24](=[O:25])[CH:23]=[C:22]([C:26]([F:28])([F:29])[F:27])[N:21]([CH3:30])[C:20]2=[O:31])=[CH:4][C:5]=1[O:10][C:11]1[CH:12]=[C:13]([OH:17])[CH:14]=[CH:15][CH:16]=1)#[N:9]

Participants

5

Reactant 2

HCID 887MethanolHCID 18759293HCID 18759293, compound

Product 1

HCID 18759300HCID 18759300, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 25134Boron tribromideSolvent

Procedure

To a solution of 57 mg of 5-fluoro-2-(3-methoxyphenoxy)-4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]cyanobenzene in 0.6 ml of chloroform, 48 μl of boron tribromide was added dropwise at 0° C. After the addition, the temperature of the reaction mixture was raised to room temperature and stirred for 1 hour. The mixture was cooled to 0° C. and 1 ml of methanol was added thereto. The solvent was removed under reduced pressure, the resultant was diluted with ethyl acetate, and then, saturated aqueous sodium bicarbonate solution was added thereto to be pH 4. The resultant was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 36 mg of 3-{2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}phenol.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe solvent was removed under reduced pressure
  4. additionthe resultant was diluted with ethyl acetate
  5. additionsaturated aqueous sodium bicarbonate solution was added
  6. extractionThe resultant was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0d4ac9474224445e9cc65e0a7ab385a4
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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