Water → 4-(2,3-Difluorophenyl)-6-(4-fluoro-2-butynyloxy)pyrimidine

HRID 1759918Notes

Reaction equation

HRID 1759918 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]#[C:18][CH2:19]O)[N:12]=[CH:11][N:10]=1.[F:21]C1(F)N(C)CCN1C.O>C(#N)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]#[C:18][CH2:19][F:21])[N:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27791112,2-Difluoro-1,3-dimethylimidazolidineHCID 225997764-(2,3-Difluorophenyl)-6-(4-hydroxy-2-butynyloxy)pyrimidine

Product 1

HCID 225997324-(2,3-Difluorophenyl)-6-(4-fluoro-2-butynyloxy)pyrimidineYield 16.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 6 ml of acetonitrile was dissolved 255 mg of 4-(2,3-difluorophenyl)-6-(4-hydroxy-2-butynyloxy)pyrimidine, to which 148 mg of 2,2-difluoro-1,3-dimethylimidazolidine was added, followed by stirring at room temperature for 24 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The resulting residue was subjected to silica gel column chromatography to give 43 mg of 4-(2,3-difluorophenyl)-6-(4-fluoro-2-butynyloxy)pyrimidine (the present compound (135)).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1ef9992579c54e5888d5f11b73407568
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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