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

HRID 75959Notes

Reaction equation

HRID 75959 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-e02d8402bf2d48dd86d4dd21e0cc7fff
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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