| Identification | Back Directory | [Name]
PYRAZIN-2-YL-HYDRAZINE | [CAS]
54608-52-5 | [Synonyms]
SELI-007
Hydrazinopyrazine
Pyrazinylhydrazine
2-Hydrazinylpyrazin
2-HYDRAZINOPYRAZINE
2-Hydrazinylpyrazine
3-Hydrazine pyrazine
PYRAZIN-2-YL-HYDRAZINE
1-(pyrazin-2-ylydrazine
Pyrazine, 2-hydrazinyl-
2-Hydrazinopyrazine,98%
2-Hydrazinopyrazine ,97%
2-Hydrazinylpyrazine HCl
2-(pyrazin-2-yl)hydrazine
2(1H)-Pyrazinone hydrazone
1-(pyrazin-2-yl) hydrazine
Pyrazin-2-yl-hydrazine ,97%
2-hydrazinylpyrazine hydrochloride
(Pyrazin-2-yl)hydrazine, 2-Hydrazino-1,4-diazine | [Molecular Formula]
C4H6N4 | [MDL Number]
MFCD04114555 | [MOL File]
54608-52-5.mol | [Molecular Weight]
110.12 |
| Chemical Properties | Back Directory | [Melting point ]
109-113℃ | [Boiling point ]
246.3±23.0 °C(Predicted) | [density ]
1.39±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [form ]
Solid | [pka]
5.10±0.20(Predicted) | [color ]
Yellow | [Water Solubility ]
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 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale yellow solid | [Uses]
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. | [Synthesis]
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). | [References]
[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 |
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