Cesium carbonate → 5-Bromo-1-(2-(tert-butyldimethylsilyloxy)ethyl)pyrimidin-2(1H)-one
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 5-bromo-2-pyrimidinone (5.3 g, 30 mmol) in N,N-dimethylformamide (50 mL) was added (2-bromoethoxy)(tert-butyl)dimethylsilane (8.5 mL, 39 mmol) and cesium carbonate (12 g, 36 mmol). The mixture was stirred at 25° C. for 3 days, then poured into aq. NaHCO3 (500 mL) and extracted with 50% EtOAc/hexane (3×200 mL). The combined extracts were washed with H2O (3×200 mL) and brine (200 mL) and then dried (Na2SO4) and concentrated to afford a brown solid. Recrystallization from EtOAc/hexane afforded the title compound as an off-white crystalline solid (6.0 g, 59% yield). MS (ESI, pos. ion.) m/z: 333 (MH+). Calc'd exact mass for C12H21BrN2O2Si: 333. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.08 (s, 6 H), 0.80 (s, 9 H), 3.81 (t, J=5.0 Hz, 2 H), 3.96 (t, J=5.0 Hz, 2 H), 8.40 (d, J=3.3 Hz, 1 H), 8.63 (d, J=3.3 Hz, 1 H).
Workup
- extractionextracted with 50% EtOAc/hexane (3×200 mL)
- washThe combined extracts were washed with H2O (3×200 mL) and brine (200 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- customto afford a brown solid
- customRecrystallization from EtOAc/hexane
Sources & evidence
- ORD record
- ord-d88844e09f1644deb51d6f0e38745190
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08314087B2
Reaction notes
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