5-Bromo-3-methoxypyrazin-2-ylamine

Bezeichnung:5-Bromo-3-methoxypyrazin-2-ylamine

CAS-Nr5900-13-0

Englisch Name:5-Bromo-3-methoxypyrazin-2-ylamine

CBNumberCB6145518

SummenformelC5H6BrN3O

Molgewicht204.02

MOL-Datei5900-13-0.mol

5-Bromo-3-methoxypyrazin-2-ylamine physikalisch-chemischer Eigenschaften

Schmelzpunkt	135-140 °C
Siedepunkt	262 ºC
Dichte	1.723
Brechungsindex	1.
Flammpunkt	112 ºC
storage temp.	2-8°C
Löslichkeit	DMSO, Methanol
pka	1.93±0.10(Predicted)
Aggregatzustand	Solid
Farbe	Off-White
InChI	1S/C5H6BrN3O/c1-10-5-4(7)8-2-3(6)9-5/h2H,1H3,(H2,7,8)
InChIKey	QDFJJHGAODFQMN-UHFFFAOYSA-N
SMILES	COc1nc(Br)cnc1N
CAS Datenbank	5900-13-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-37/38-41
S-Sätze:	26-39
WGK Germany	3
HS Code	2933990099
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

5-Bromo-3-methoxypyrazin-2-ylamine Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Off-White Solid
Verwenden
5-Bromo-3-methoxy-2-pyrazinamine is an intermediate in the preparation of N-pyrazinylbenzenesulfonamides used in treatment of chemokine mediated diseases such as asthma.
Synthese

124-41-4

24241-18-7

5900-13-0

1. A 30% w/w methanolic solution of sodium methanolate (8.4 mL, 44.8 mmol) was slowly added to a stirring suspension of 3,5-dibromo-2-aminopyrazine (10 g, 39.5 mmol) in anhydrous methanol (40 mL). 2. The reaction mixture was heated to reflux and the reaction was maintained for 3 h. 3. Upon completion of the reaction, the reaction was cooled to room temperature and concentrated to 1/3 of the original volume by rotary evaporation. 4. The concentrated reaction mixture was partitioned between dichloromethane (DCM) and saturated aqueous sodium bicarbonate (NaHCO3).5 The organic and aqueous layers were separated and the organic phase was washed three times with saturated aqueous NaHCO3.6 The aqueous phases were combined and back-extracted three times with DCM.7 All the organic phases were combined, washed with saturated saline, dried with anhydrous sodium sulfate, filtered, and concentrated to give 5 mL of the reaction mixture.8 The reaction mixture was then dried. dried, filtered and concentrated to give 5-bromo-3-methoxypyrazin-2-amine (8.1 g). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.64 (s, 1H), 4.79 (br s, 2H), 4.01 (s, 3H).
Einzelnachweise
[1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 9, p. 981 - 986
[2] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1149 - 1154
[3] Patent: US2013/210818, 2013, A1. Location in patent: Paragraph 0384
[4] Patent: WO2014/68171, 2014, A1. Location in patent: Page/Page column 27
[5] Patent: WO2009/115572, 2009, A2. Location in patent: Page/Page column 116

5-Bromo-3-methoxypyrazin-2-ylamine Upstream-Materialien And Downstream Produkte

5-Bromo-3-methoxypyrazin-2-ylamine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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