Dimethylformamide → 2-(Cyclohexylmethoxy)pyrimidine-4-carbaldehyde

HRID 63352Notes

Reaction equation

HRID 63352 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN([CH:18]=[O:19])C>C1COCC1>[CH:1]1([CH2:7][O:8][C:9]2[N:10]=[C:11]([CH:18]=[O:19])[CH:12]=[CH:13][N:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 866946672-(Cyclohexylmethoxy)pyrimidine

Product 1

HCID 866946682-(Cyclohexylmethoxy)pyrimidine-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Knochel-Hauser reagent (2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex) is added to a mixture of 2-(cyclohexylmethoxy)pyrimidine in THF at −78° C., stirred for 15 min, then DMF is added. The reaction mixture is stirred at −30° C., quenched by aqueous NH4Cl, extracted with ethyl acetate. Combined organic layers are dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 2-(cyclohexylmethoxy)-pyrimidine-4-carbaldehyde.

Workup

  1. stirringThe reaction mixture is stirred at −30° C.
  2. customquenched by aqueous NH4Cl
  3. extractionextracted with ethyl acetate
  4. dry with materialCombined organic layers are dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2973922bc5dc42598ac42412f248742d
Source dataset
uspto-grants-2016_09
Patent number
US09447078B2

Reaction notes

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