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Chemical Structure| 369638-69-7 Chemical Structure| 369638-69-7

Structure of 369638-69-7

Chemical Structure| 369638-69-7

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Product Details of [ 369638-69-7 ]

CAS No. :369638-69-7
Formula : C10H14BrN3O2
M.W : 288.14
SMILES Code : O=C(OC(C)(C)C)NC1=NC=C(CBr)N=C1
MDL No. :MFCD10574803
InChI Key :FPWNVMNGKNLYSC-UHFFFAOYSA-N
Pubchem ID :45073740

Safety of [ 369638-69-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3259
Packing Group:

Application In Synthesis of [ 369638-69-7 ]

* 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.

  • Downstream synthetic route of [ 369638-69-7 ]

[ 369638-69-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 369638-68-6 ]
  • [ 369638-69-7 ]
YieldReaction ConditionsOperation in experiment
77% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 100℃; for 4.0h;Product distribution / selectivity; Step 2: To a solution of <strong>[369638-68-6](5-methyl-pyrazin-2-yl)-carbamic acid tert-butyl ester</strong> (from above and from example 21, step 1, 12.9 g, 61.6 mmol) and AIBN (10.1 g, 61 mmol) in CCl4 (100 mL) was added NBS (11 g, 61.6 mmol) and the reaction mixture was stirred at 100 C. for 4 h. The reaction mixture was filtered, washed with CH2Cl2 and concentrated in vacuo. Purification by chromatography (silica, 4:5:1 CH2Cl2:hexanes:ethyl acetate) with repurification of mixed fractions by chromatography (silica, 4:5:1 CH2Cl2:hexanes:ethyl acetate) afforded a total of (5-bromomethyl-pyrazin-2-yl)-carbamic acid tert-butyl ester (13.6 g, 77%): 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.57 (s, 9H) 4.55 (s, 2H) 8.15 (s, 1H) 8.34 (d, J=1.51 Hz, 1H) 9.28 (d, J=1.51 Hz, 1H).
75% With N-Bromosuccinimide;2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 4.0h; B. tert-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate; To a solution <strong>[369638-68-6]tert-butyl 5-methylpyrazin-2-ylcarbamate</strong> (500 mg, 2.39 mmol) in CC (8.0 niL) were added NBS(446 mg, 2.51 mmol) and AIBN (117 mg, 0.72 mmol). The reaction mixture was stirred for 4 hours at 80 C after which, it was partitioned between CH2CI2 and water. The organic layer was separated and the aqueous layer was extracted with CH2CI2. The combined organic extracts were washed with brine, dried over MgS04, celite filtered and concentrated under reduced pressure. The crude product was purified by flashchromatography using (10% Ethyl acetate/Hexane) as a solvent to afford title compound (520 mg, 75% yield). 1H NMR (600 MHz, CDC13) delta 9.29 (s, 1H), 8.95 (s, 1H), 8.37 (s, 1H), 4.38 (s, 2H), 1.57 (s, 9H). MS m/z : 288 [M+l].
With N-Bromosuccinimide; sodium hydrogencarbonate; In tetrachloromethane; at 80℃; for 12.0h; Intermediate: te/t-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate (29b)BocHNgammaN.(29b)To a solution of te/t-butyl 5-methylpyrazin-2-ylcarbamate (29a) (100 g, 0.48 mol) inCCU (40 mL) was added NaHCO,? followed by AZ-bromosuccinimide (130 g, 0.57 mol). The resulting mixture was heated to reflux at 800C for 12 hours then cooled to room temperature. The reaction mixture was filtered through Cehte and the filtrate was concentrated in vacuo. The crude product was chromatographed (SiO?; 5 % EtOAc in CHCI3) to give tert-buty 5-{bromomethyi)pyrazm-2-y.carbamate (29b).
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 85℃; for 4.0h;Inert atmosphere; Step 2. tert-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate:_A solution of <strong>[369638-68-6]tert-butyl 5-methylpyrazin-2-ylcarbamate</strong> (2.79 g, 13.33 mmol), NBS (2.61 g, 14.67 mmol) and AlBN (0.219 g, 1.33 mmol) in CCl4 (45 mL) was purged with Argon, then the solution was heated with 85 C. oil bath for 4 h. The reaction mixture was cooled to room temperature, concentrated and the residue was redissolved in EtOAc (?50 mL), washed with dilute aqueous NaOH twice (10 mL 1 N NaOH diluted in 20 mL H2O), brine (30 mL), dried (Na2SO4) and concentrated. The residue was further purified by flash chromatography on silica gel eluted with gradient EtOAc/CH2Cl2 (0-30%) and tert-butyl 5-(bromomethyl)pyrazin-2-ylcarbamate was obtained in off-white solid. LCMS (m/z): 288.1/290.1 (MH+), 0.82 min; 1H NMR (400 MHz, CDCl3) delta ppm 9.26 (s, 1H), 8.32 (d, J=1.2 Hz, 1H), 7.62 (br. s., 1H), 4.56 (s, 2H), 1.56 (s, 9H).

  • 2
  • [ 369638-68-6 ]
  • C10H13Br2N3O2 [ No CAS ]
  • [ 369638-69-7 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;Heating / reflux; (2) 158 g of the Compound [1-1] obtained in (1) above was dissolved in 2 L of carbon tetrachloride, then 267 g ofN-bromosuccinimide and 25 g of azobisisobutyronitrile were added to the solution, and the mixture was stirred overnight under overheating reflux. The obtained reaction solution was cooled to room temperature, and the insolubles were removed by filtration under reduced pressure. The filtrate was concentrated, and a monobromide product [1-2-1] was obtained as a mixture of a dibromide product [1-2-2] and Compound [1-1]. The monobromide product [1-2-1] was used in the subsequent reaction without further purification. [Show Image] The spectral data of the compound represented by the above Formula [1-2-1] is presented below. 1H-NMR (CDCl3) delta: 9.27 (1H, s), 8.33 (1H, s), 7.91 (1H, brs), 4.55 (2H, s), 1.55 (9H, s). mass: 288, 300 (M+1)+.
 

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