Tetrahydrofuran → 1-(5-Fluoropyrimidin-2-yl)ethanone

HRID 2189920Notes

Reaction equation

HRID 2189920 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5](C#N)=[N:6][CH:7]=1.[CH2:10]1[CH2:14][O:13]CC1.C[Mg+].[Br-]>CCOCC>[F:1][C:2]1[CH:3]=[N:4][C:5]([C:14](=[O:13])[CH3:10])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 441818675-Fluoropyrimidine-2-carbonitrileHCID 178418689HCID 178418689, compound

Product 1

HCID 509948151-(5-Fluoropyrimidin-2-yl)ethanoneYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottom-flask containing 5-fluoropyrimidine-2-carbonitrile (Method 59, 1.50 g, 12.19 mmol) was charged with anhydrous THF (30 ml) under N2. The solution was cooled to 0° C., and a solution of MeMgBr (4.90 ml of a 3.0 M solution in ether, 14.62 mmol) was added dropwise. After 2 hours at 0° C., the reaction mixture was quenched with ice water and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness to give the title compound as an oil (0.778 g, yield 46%). GC-MS, 140 (M); 1H NMR (CDCl3) δ 8.65 (s, 2H), 2.65 (s, 2H).

Workup

  1. customthe reaction mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ae0e849e8bcb46b38d1514d564efacc6
Source dataset
uspto-grants-2012_12
Patent number
US08324252B2

Reaction notes

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