Dimethylformamide → HCID 86760400, compound

HRID 348487Notes

Reaction equation

HRID 348487 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14]([S:17]([O-:19])=[O:18])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[Na+].Br[CH2:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:24].[CH3:31]N(C=O)C>C(OCC)(=O)C.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([CH3:31])=[N:13][C:14]([S:17]([CH2:22][C:23](=[O:24])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:19])=[O:18])=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6259Phenacyl bromideHCID 23716541HCID 23716541, compound

Product 1

HCID 86760400HCID 86760400, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium 5-(4-fluorophenylcarbamoyl)pyrimidine-2-sulfinate (76 mg, 0.24 mmol) in 2 mL of DMF was treated with 2-bromoacetophenone (48 mg, 0.24 mmol) and stirred at ambient temperature for 3 days. The solution was then diluted with 15 mL ethyl acetate and 5 mL hexane and sequentially washed with 2×5 mL portions of 0.1 M HCl and 5 mL of water. The organic phase was dried using Na2SO4, concentrated and the resultant oil chromatographed through SiO2 (2–5% MeOH/dichloromethane). Recrystallization in ethyl acetate/hexane yielded 26 mg (27%) of the titled compound as yellowish needles. ApcI-MS m/z 414 (MH+), 412 (M−H−).

Workup

  1. washsequentially washed with 2×5 mL portions of 0.1 M HCl and 5 mL of water
  2. customThe organic phase was dried
  3. concentrationconcentrated
  4. customthe resultant oil chromatographed through SiO2 (2–5% MeOH/dichloromethane)
  5. customRecrystallization in ethyl acetate/hexane

Sources & evidence

ORD record
ord-ddfe8006141c42c991d85ef48d5e2f32
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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