Ammonium Chloride → HCID 68289638, compound

HRID 878781Notes

Reaction equation

HRID 878781 reaction equation
[CH3:1][S:2][C:3]1C=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][N:4]=1.[CH:11]1([Mg]Br)[CH2:13][CH2:12]1.[Cl-].[NH4+:17]>O1CCCC1>[CH:11]1([CH:9]([C:6]2[CH:7]=[N:17][C:3]([S:2][CH3:1])=[N:4][CH:5]=2)[OH:10])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 450837916-(Methylthio)-3-pyridinecarboxaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 68289638HCID 68289638, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(methylthio)pyridine-5-carbaldehyde (2000 mg, 12.97 mmol) in tetrahydrofuran (20 mL) was added a solution of 0.5 mol/L cyclopropylmagnesium bromide in tetrahydrofuran (28.6 mL) at −40° C. under argon atmosphere. The reaction solution was stirred at the same temperature for 10 minutes, and then slowly warmed to 0° C. and stirred for 1 hour. To the reaction solution was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30→60:70) to give cyclopropyl[2-(methylthio)pyrimidin-5-yl]methanol (822 mg, 32%) as a colorless oil.

Workup

  1. stirringstirred for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30→60:70)

Sources & evidence

ORD record
ord-c483cc2b908b4a009037e7fdc5ff34c5
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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