2-chloro-N-methoxy-N-methylpyrimidine-4-carboxamide → 1-(2-Chloropyrimidin-4-yl)ethanone

HRID 1039922Notes

Reaction equation

HRID 1039922 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](N(OC)C)=[O:9])[CH:5]=[CH:4][N:3]=1.[CH3:14][Mg]Cl>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8](=[O:9])[CH3:14])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 772313502-chloro-N-methoxy-N-methylpyrimidine-4-carboxamideHCID 178418332HCID 178418332, compound

Product 1

HCID 446138781-(2-Chloropyrimidin-4-yl)ethanoneYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-chloro-N-methoxy-N-methylpyrimidine-4-carboxamide (75 mg, 0.372 mmol) in THF (3 mL) at −78° C. under a nitrogen atmosphere was added methyl magnesium chloride (3.0 M in THF, 0.124 mL, 0.372 mmol) dropwise. The solution was warmed to room temperature for 1 hr. The solution was diluted with EtOAc, washed with 1 N the organic layer was neutralized with saturated aqueous NaHCO3, dried with MgSO4, filtered, and concentrated to dryness. Purification on silica gel by flash chromatography (0-100% EtOAc/hexanes) afforded 1-(2-chloropyrimidin-4-yl)ethanone (45 mg, 0.29 mmol, 77% yield). 1H NMR (500 MHz, CDCl3) δ 8.86 (d, J=4.9, 1H), 7.83 (d, J=4.9, 1H), 2.71 (s, 3H).

Workup

  1. washwashed with 1 N the organic layer
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customPurification on silica gel by flash chromatography (0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-986d0300866643d68aa3d0e22b5e2826
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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