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

HRID 1592196Notes

Reaction equation

HRID 1592196 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-5320f5275d7445e798848df791317c87
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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