Tetrahydrofuran → 1-(5-Bromopyrimidin-2-yl)ethan-1-one

HRID 1046102Notes

Reaction equation

HRID 1046102 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](C#N)=[N:6][CH:7]=1.C[Mg+].[Br-].[CH2:13]1[CH2:17][O:16]CC1>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:17](=[O:16])[CH3:13])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 6865465-Bromopyrimidine-2-carbonitrileHCID 178418689HCID 178418689, compound

Product 1

HCID 534880641-(5-Bromopyrimidin-2-yl)ethan-1-oneYield 30.2%

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-bromopyrimidine-2-carbonitrile (300 mg, 1.63 mmol) in THF (20 mL) was added MeMgBr (5.43 mL, 16.3 mmol) at −78° C. under nitrogen. The solution was stirred at −78° C. for 20 min., quenched with satd aq NH4Cl, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give an oil, which was purified by prep TLC (3:1 PE/EtOAc) to give 1-(5-bromopyrimidin-2-yl)ethanone (99 mg, yield 30.2%). 1H NMR (CDCl3): δ2.70 (s, 3H), 8.90 (m, 2H).

Workup

  1. customquenched with satd aq NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto give an oil, which
  6. customwas purified by prep TLC (3:1 PE/EtOAc)

Sources & evidence

ORD record
ord-d3727f56287c4a5085a760fc8f17c612
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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