Hydrochloric Acid → (6-(((Tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)(cyclopropyl)methanone
Reaction equation
[Si:1]([O:18][CH2:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([C:26]#N)[CH:21]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]1([Mg]Br)[CH2:30][CH2:29]1.Cl.C1C[O:37]CC1>>[Si:1]([O:18][CH2:19][C:20]1[N:25]=[CH:24][N:23]=[C:22]([C:26]([CH:28]2[CH2:30][CH2:29]2)=[O:37])[CH:21]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Procedure
Under a nitrogen atmosphere, to a solution of 6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidine-4-carbonitrile (11.3 g) in THF (100 mL) was added 0.70 M cyclopropylmagnesium bromide (86 mL) at 0° C., and the mixture was directly stirred for 30 min. To the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution 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
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-7617a588e7334074beae765eccf7d4e1
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382188B2
Reaction notes
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