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Chemical Structure| 925678-00-8 Chemical Structure| 925678-00-8

Structure of 925678-00-8

Chemical Structure| 925678-00-8

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Product Details of [ 925678-00-8 ]

CAS No. :925678-00-8
Formula : C4H3ClIN3
M.W : 255.44
SMILES Code : NC1=NC(Cl)=C(I)N=C1
MDL No. :MFCD19687957
InChI Key :YEBDYUMXHLRMBW-UHFFFAOYSA-N
Pubchem ID :59457651

Safety of [ 925678-00-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H311-H331
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 925678-00-8 ]

* 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 [ 925678-00-8 ]

[ 925678-00-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 33332-28-4 ]
  • [ 925678-00-8 ]
YieldReaction ConditionsOperation in experiment
88% With N-iodo-succinimide; In dimethyl sulfoxide; at 25℃; To a solution of 6-chloropyrazin-2-amine (10 g, 77.2 mmol) in DMSO (100 mL) was added NIS (17.4 g, 77.2 mmol) and the solution was stirred at 25C overnight. After the mixture was poured into water and extracted with EtOAc, the organic solutions were collected, washed with brine, dried over NaS04 and filtered. The filtrate was evaporated under reduced pressure and the residue purified by silica gel chromatograph using Petroleum Ether:EtOAc 1 :4 as eluting solvents to afford 6-chloro-5-iodopyrazin-2-amine as a yellow solid (17.2 g, 88%). MS (ESI) m/z: 255 [M+H]+.
76% With N-iodo-succinimide; In water; dimethyl sulfoxide; at 0℃; for 72h; 6-Chloro-5-iodo-4-ylpyrazin-2-amine To a O0C cooled stirred solution of <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (3 g, 23 mmol) in a mixture of DMSO (90 mL) and water (2.2 mL), was added Lambda/-iodosuccinimide (5.2 g, 23 mmol) in EPO <DP n="54"/>portions. After stirring for 72h, the mixture was poured into water, extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (98:2 dichloromethane/methanol) furnished the title compound as a yellow solid (4.43 g, 76%). delta 1H-NMR (CDCI3): 7.73 (s, 1H), 4.72 (s, 2H).ESI/MS (m/e, %): 255 [(M+1) C4H3CIIN3].
75% With Iodine monochloride; potassium carbonate; In methanol; dichloromethane; at 0 - 20℃; To a mixture of compound 9 (312.0 g, 2A mol) and K2C03 (664.0 g, 4.8 mol) in MeCH(1.0 L) was dropwise added lCl (704.0 g, 4.3 mol in 1.0 L of DCM) over 2 hours0C. Then the reaction mixture was stirred at room temperature overnight. Thereaction was quenched with Na2SO3 aqueous solution (2M, 1 .5 L). The mixture was extracted with DCM (1.0 L x 3). The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purifiedcolumn chromatography on silica gel (PEIEA = 10/1 to 4/1) to afford compound(460 g, 75% yield) as a solid.1HNMR (400 MHz, DMSQd6): 7.68 (s, 1H), 7.07 (s 2H). MS Calcd.: 255 MS Found: 256 ([M+Hfl.
75% With Iodine monochloride; potassium carbonate; In methanol; dichloromethane; at 0 - 20℃; To a mixture of compound 9 (312.0 g, 2.4 mol) and K2CO3 (664.0 g, 4.8 mol) in MeOH (1.0 L) was dropwise added IC1 (704.0 g, 4.3 mol in 1.0 L of DCM) over 2 hours at 0C. Then the reaction mixture was stirred at room temperature overnight. The reaction was quenched with NaiSC aqueous solution (2M, 1.5 L). The mixture was extracted with DCM (1.0 L x 3). The combined organic phases were dried over anhydrous Na2S04, filtered and concentrated. The crude product was purified by column chromatography on silica gel (PE/EA = 10/1 to 4/1) to afford compound 10 (460 g, 75% yield) as a solid. 1HNMR (400 MHz, DMSO- 6): delta 7.68 (s, 1H), 7.07 (s, 2H). MS Calcd.: 255 MS Found: 256 ([M+H]+).
42% With N-iodo-succinimide; In acetonitrile; at 0 - 20℃; Step-1: Synthesis of 6-chloro-5-iodopyrazin-2-amine To a stirred solution of <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (2.0 g, 1.0 eq., 15.50 mmol) in acetonitrile (20 mL) was added NIS (3.46 g, 1.0 eq., 15.50 mmol) at 0 C. The reaction was allowed to stir at RT. Progress of the reaction was monitored by TLC and LCMS After completion of the reaction the solvent was evaporated under vacuum and the solid was extracted using ethyl acetate (3*100 mL). The combined organic layers were washed (brine), dried (anhydrous Na2SO4) and concentrated under vacuum to get the solid which was purified by normal phase column chromatography to get the desired product (1.7 g, 42%).
With N-iodo-succinimide; In water; dimethyl sulfoxide; at 0℃; for 72h;Darkness; Step 1 To <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (1eq) in DMSO and water is added at 0C NIS (1.1 eq) in 3 portions. The mixture is stirred in the dark for 72 h. The mixture is poured into water, extracted with EtOAe and-evaporated. The crude material is purified via flash column chromatography.
With N-iodo-succinimide; In dimethyl sulfoxide; at 20℃; for 48h; A solution of 6-chloropyrazin-2-amine (10.0 g, 77 mmol) in DMSO (100 ml) was treated with 1-iodopyrrolidine-2,5-dione (20.84 g, 93 mmol). The reaction mixture was stirred at RT for 2 days and then added to water (800 ml). The pH was adjusted to pH 8-9 using a sat. NaHCO3 solution and the resulting suspension was filtered, washing with water (*3) and dried under vacuum to afford the titled compound as an orange solid; LC-MS Rt=0.83 mins; [MeCN+H]+ 296.0, Method 2 minLowpH.

 

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