2-Hydrazinopyrazine

Bezeichnung:2-Hydrazinopyrazine

CAS-Nr54608-52-5

Englisch Name:2-Hydrazinopyrazine

CBNumberCB9692578

SummenformelC4H6N4

Molgewicht110.12

MOL-Datei54608-52-5.mol

2-Hydrazinopyrazine physikalisch-chemischer Eigenschaften

Schmelzpunkt	109-113℃
Siedepunkt	246.3±23.0 °C(Predicted)
Dichte	1.39±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Aggregatzustand	Solid
pka	5.10±0.20(Predicted)
Farbe	Yellow
Wasserlöslichkeit	Slightly soluble in water.
InChI	InChI=1S/C4H6N4/c5-8-4-3-6-1-2-7-4/h1-3H,5H2,(H,7,8)
InChIKey	IVRLZJDPKUSDCF-UHFFFAOYSA-N
SMILES	C1(NN)=NC=CN=C1

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-41-36/37/38
S-Sätze:	26-39-36/37/39
HS Code	29339900

Gefahreninformationscode (GHS)

2-Hydrazinopyrazine Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Pale yellow solid
Verwenden
Triazolo[4,3-a]pyrazine 7-oxide, 3-β-D-ribofuranosyl-1,2,4-triazolo[4,3-a]pyrazine, monohydrazones of pyridine, pyrazine, phenylglyoxal were synthesised from 2-Hydrazinopyrazine.
Application
2-Hydrazinopyrazine is used as a reagent in the synthesis of Sitagliptin (S491000, H3PO4) and its analogs. Sitagliptin is a trizolopyrazine dipeptidyl peptidase IV inhibitor that has recently been approved for the therapy of type II diabetes.
Synthese

14508-49-7

54608-52-5

Step 1: Synthesis of pyrazine-2-hydrazine from 2-chloropyrazine. 2-Chloropyrazine (2.0 g, 17.5 mmol) was slowly added dropwise to 35% aqueous hydrazine hydrate (25.8 g, 97.8 mmol) at 63-65°C, and the rate of acceleration of the dropwise addition was strictly controlled so as to maintain the temperature of the reaction not exceeding 65°C. After the dropwise addition was completed, the reaction mixture was heated further up to 65°C and kept at this temperature. The reaction mixture was stirred overnight and cooled to room temperature. The solvent was removed by distillation under reduced pressure to give the product pyrazine-2-hydrazine (1.5 g, 75% yield) as a yellow powder. Mass spectrometry (ESI) analysis: calculated value C4H6N4[M]: 110.1; measured value: 111.4 [M+H]+.1H NMR (400 MHz, CD3OD) δ 8.10 (d, J=1.6 Hz, 1H), 8.00 (dd, J=3.2,1.6 Hz, 1H), 7.73 (d, J=3.2 Hz, 1H).
Einzelnachweise
[1] Patent: WO2016/100349, 2016, A2. Location in patent: Paragraph 0204
[2] Letters in Organic Chemistry, 2013, vol. 10, # 5, p. 348 - 352
[3] Patent: WO2013/71697, 2013, A1. Location in patent: Paragraph 00198
[4] Patent: US2014/228361, 2014, A1. Location in patent: Paragraph 0279-0280
[5] Patent: CN106749262, 2017, A. Location in patent: Paragraph 0035

2-Hydrazinopyrazine Upstream-Materialien And Downstream Produkte

2-Hydrazinopyrazine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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