N-Methoxy-N-methylpyrimidine-5-carboxamide → (4-Chlorophenyl)(pyrimidin-5-yl)methanone

HRID 627500Notes

Reaction equation

HRID 627500 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.CON(C)[C:13]([C:15]1[CH:16]=[N:17][CH:18]=[N:19][CH:20]=1)=[O:14]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]([C:15]2[CH:16]=[N:17][CH:18]=[N:19][CH:20]=2)=[O:14])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 66575045N-Methoxy-N-methylpyrimidine-5-carboxamideHCID 178478191HCID 178478191, compound

Product 1

HCID 13645652(4-Chlorophenyl)(pyrimidin-5-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-chlorophenylmagnesium bromide (1 M in Et2O, 4.53 mL, 4.53 mmol) was added to a solution of crude N-methoxy-N-methylpyrimidine-5-carboxamide (505 mg, 3.02 mmol, Intermediate 28, step a) in THF at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The reaction was quenched by addition of saturated aqueous NH4Cl, diluted with water, and extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, gradient 1-5% MeOH-DCM), affording impure title compound which was used without further purification.

Workup

  1. customThe reaction was quenched by addition of saturated aqueous NH4Cl
  2. additiondiluted with water
  3. extractionextracted three times with EtOAc
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica gel, gradient 1-5% MeOH-DCM)

Sources & evidence

ORD record
ord-b4a0921e7da14144b5efa9d59312ed93
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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