Identification | Back Directory | [Name]
3,5-Dibromo-2-chloropyrazine | [CAS]
1082843-70-6 | [Synonyms]
3,5-Dibromo-2-chloropyrazine 2-Chloro-3,5-dibroMopyrazine Pyrazine, 3,5-dibromo-2-chloro- 3,5-Dibromo-2-chloropyrazine ISO 9001:2015 REACH | [EINECS(EC#)]
201-903-5 | [Molecular Formula]
C4HBr2ClN2 | [MDL Number]
MFCD13193367 | [MOL File]
1082843-70-6.mol | [Molecular Weight]
272.33 |
Chemical Properties | Back Directory | [Boiling point ]
261℃ | [density ]
2.265 | [Fp ]
112℃ | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
-6.65±0.10(Predicted) | [Appearance]
White to off-white Solid |
Hazard Information | Back Directory | [Uses]
3,5-Dibromo-2-chloropyrazine is an intermediate used for the 1) preparation of a number of salts of fused pyrazine derivative for treatment of degenerative and inflammatory diseases, 2) preparation of a number of pyridine and pyrazi ne derivatives as protein kinase modulators for the treatment of CDK9-mediated diseases.
| [Uses]
An intermediate used for the 1) preparation of a number of salts of fused pyrazine derivative for treatment of degenerative and inflammatory diseases, 2) preparation of a number of pyridine and pyrazine derivatives as protein kinase modulators for the treatment of CDK9-mediated diseases. | [Synthesis]
General procedure for the synthesis of 3,5-dibromo-2-chloropyrazine from 2-amino-3,5-dibromopyrazine: titanium(IV) chloride (174 g, 926 mmol) was added to a solution of 2-amino-3,5-dibromopyrazine (234 g, 932 mmol) in dichloromethane (DCM, 700 mL), followed by slow addition of tert-butyl nitrite (572 g, 5.55 mol). The reaction mixture was stirred at room temperature for 2 h and then the reaction was quenched with water (500 mL). The reaction mixture was extracted with dichloromethane (3 × 500 mL). The organic layers were combined and concentrated under reduced pressure. Purification of the residue by rapid column chromatography on silica gel (eluent: ethyl acetate/petroleum ether, 1:50 v/v) afforded 3,5-dibromo-2-chloropyrazine (90d) as a colorless oil (210 g, 83% yield). Mass spectrum (LCMS, ESI positive ion mode): calculated value C4HBr2ClN2 [M+H]+: 272.8, measured value: 272.6. | [References]
[1] Patent: US2014/364414, 2014, A1. Location in patent: Paragraph 0945; 0952-0953 [2] Patent: US2009/286798, 2009, A1. Location in patent: Page/Page column 26-27 [3] Patent: US2011/118269, 2011, A1. Location in patent: Page/Page column 14 [4] Patent: WO2014/1377, 2014, A1. Location in patent: Page/Page column 153; 154 |
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