2-Bromo-1-methyl-1H-imidazole → HCID 81675572, compound

HRID 627501Notes

Reaction equation

HRID 627501 reaction equation
C([Mg]Br)C.Br[C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][N:10]=1.CON(C)[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[N:21][CH:22]=1)=[O:16]>C(Cl)Cl>[CH3:11][N:7]1[CH:8]=[CH:9][N:10]=[C:6]1[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[N:21][CH:22]=1)=[O:16]

Participants

5

Reactant 3

HCID 27732622-Bromo-1-methyl-1H-imidazoleHCID 66575045N-Methoxy-N-methylpyrimidine-5-carboxamideHCID 178418443HCID 178418443, compound

Product 1

HCID 81675572HCID 81675572, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethylmagnesium bromide (3 M in Et2O, 1.05 mL, 3.14 mmol) was added dropwise to a solution of 2-bromo-1-methyl-1H-imidazole (505 mg, 3.14 mmol) in DCM (6 mL) under a nitrogen atmosphere. The mixture was stirred at room temperature 30 min, then was cooled in an ice bath prior to addition of a solution of N-methoxy-N-methylpyrimidine-5-carboxamide (419 mg, 2.51 mmol, Intermediate 28, step a) in DCM (1 mL). The resulting suspension was stirred at room temperature for 24 hours. The reaction was quenched by addition of saturated aqueous NH4Cl, diluted with water, and extracted three times with DCM. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, gradient 0-60% CH3CN-DCM), affording the title compound.

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringThe resulting suspension was stirred at room temperature for 24 hours
  3. customThe reaction was quenched by addition of saturated aqueous NH4Cl
  4. additiondiluted with water
  5. extractionextracted three times with DCM
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (silica gel, gradient 0-60% CH3CN-DCM)

Sources & evidence

ORD record
ord-cb68ce33331e4d45b9d117c962ee487f
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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