Hydrochloric Acid → Cyclopropyl(6-methoxypyrimidin-4-yl)methanone

HRID 709607Notes

Reaction equation

HRID 709607 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([C:9]#N)[CH:4]=1.[CH:11]1([Mg]Br)[CH2:13][CH2:12]1.Cl.C(=O)([O-])[OH:18].[Na+]>C1COCC1>[CH:11]1([C:9]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=2)=[O:18])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 592380226-Methoxypyrimidine-4-carbonitrileHCID 178418630HCID 178418630, compound

Product 1

HCID 91618935Cyclopropyl(6-methoxypyrimidin-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, to a solution of 6-methoxypyrimidine-4-carbonitrile (6.00 g) in THF (120 mL) was added dropwise a 0.52 M solution of cyclopropylmagnesium bromide in THF (215 mL) at 0° C., and the mixture was stirred at 0° C. for 1 hr. 6N Hydrochloric acid (60 mL) was added to the reaction mixture at 0° C., and the mixture was stirred at room temperature for 15 min. The reaction mixture was neutralized with sodium hydrogen carbonate (35.0 g), and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound as a brown oil. This compound was used for the next step without further purification.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a2391facef1a4361924c5d803b42405e
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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