Acetonitrile → 6-(((Tert-butyldiphenylsilyl)oxy)methyl)pyrimidine-4-carbonitrile

HRID 1049492Notes

Reaction equation

[Si:1]([O:18][CH2:19]C1N=CC=C(Cl)N=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.[N:27]12[CH2:34][CH2:33][N:30](C[CH2:32]1)CC2.[C:35](#[N:37])[CH3:36]>[C-]#N.C([N+](CC)(CC)CC)C>[Si:1]([O:18][CH2:19][C:35]1[N:37]=[CH:32][N:27]=[C:34]([C:33]#[N:30])[CH:36]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([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]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Under a nitrogen atmosphere, to a solution of (((tert-butyldiphenylsilyl)oxy)methyl)-6-chloropyrimidine (18.6 g) and 1,4-diazabicyclo[2.2.2]octane (8.18 g) in acetonitrile (97 mL) was added tetraethylammonium cyanide (7.59 g) at room temperature, and the mixture was stirred at 50° C. for 30 min. The solvent of the reaction mixture was evaporated under reduced pressure and the insoluble solid was removed by filtration. The solvent of the filtrate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (11.3 g) as a colorless oil.

Workup

customThe solvent of the reaction mixture was evaporated under reduced pressure
customthe insoluble solid was removed by filtration
customThe solvent of the filtrate was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-1fca41f14ded4844903575ebd7c88237
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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