2-Cyanopyrimidine → 1-(Pyrimidin-2-yl)ethan-1-one
Reaction equation
C([C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#N.[CH3:9][Mg]Br.C(Cl)(Cl)Cl.[CH3:16][OH:17]>C1COCC1.O>[N:4]1[CH:5]=[CH:6][CH:7]=[N:8][C:3]=1[C:16](=[O:17])[CH3:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-cyano-pyrimidine (10.0 g, 95.2 mmol) in THF (100 mL) was cooled to −5° C. and treated with a 3 M solution of methyl magnesium bromide in THF (38.0 mL, 98.4 mmol). The reaction was stirred at 0° C. for two hours until completion was observed by TLC (chloroform/methanol, 9:1). The reaction mixture was poured in water; the pH was adjusted to 5-6 and the aqueous layer was extracted with ethyl acetate (3×150 mL). The combined organic layers were concentrated under reduced pressure and the crude compound was purified by column chromatography, eluting with chloroform to afford the target compound (6.5 g, 48%).
Workup
- extractionthe aqueous layer was extracted with ethyl acetate (3×150 mL)
- concentrationThe combined organic layers were concentrated under reduced pressure
- customthe crude compound was purified by column chromatography
- washeluting with chloroform
Sources & evidence
- ORD record
- ord-0688f7242006440f84ee49ea5620c741
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809525B2
Reaction notes
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