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CAS No. : | 694-32-6 | MDL No. : | MFCD00800601 |
Formula : | C4H8N2O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JTPZTKBRUCILQD-UHFFFAOYSA-N |
M.W : | 100.12 | Pubchem ID : | 567600 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20℃; | Step 1: Synthesis of 5- ((1H-imidazol- 1 -yl)methyl)-2 -bromopyridine. The starting material 2-bromo-5-(bromomethyl)pyridine was synthesized according to a published protocol (Tetr. Lett. 2002, 43, 1697). To a 50 mL round bottom flask containing 1-methyl-2-imidazolidinone (250 mg, 2.5 mmol) and Nail 60%dispersion in mineral oil (110 mg, 2.75 mmol, 1.1 eq) at 0C was added 3 mL of DriSolv DMF. The reaction turned into a cloudy white solid, then warmed to room temperature, and stirred for an hour. 2-bromo-5-(bromomethyl)pyridine (750 mg, 1.2 mmol, 3 eq) was dissolved in 1 mL of DriSolv DMF and the reaction was stirred overnight at room temperature. The reaction wasconcentrated in vacuo, dissolved in EtOAc and a saturated solution of NH4C1, and extracted. The organic layer was concentrated in vacuo, and purified by automated chromatography to yield 173 mg (26%) of a light brown oil R 0.15 in 75% EtOAc in hexanes 1% MeOH). ‘H NMR (600 MHz, CD3OD) d 8.26 (d, Jz 2.4 Hz, 1H), 7.62 (dd, J 8.2, 2.5 Hz, 1H), 7.56 (d, J 8.2 Hz, lET), 4.33 (s,2H), 3.36 - 3.31 (m, 2H), 3.28 - 3.23 (m, 2H), 2.77 (s, 3ET). 13C NMR (151 MHz, CD3OD) d 150.70, 141.72, 140.28, 134.46, 129.45, 45.97, 45.95, 43.46, 31.40. |
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