TERT-BUTYL 3-BROMO-5,6-DIHYDRO-[1,2,4]TRIAZOLO[4,3-A]PYRAZINE-7(8H)-CARBOXYLATE synthesis
- Product Name:TERT-BUTYL 3-BROMO-5,6-DIHYDRO-[1,2,4]TRIAZOLO[4,3-A]PYRAZINE-7(8H)-CARBOXYLATE
- CAS Number:723286-80-4
- Molecular formula:C10H15BrN4O2
- Molecular Weight:303.16
![5,6-DIHYDRO-8H-[1,2,4]TRIAZOLO[4,3-A]PYRAZINE-7-CARBOXYLIC ACID TERT-BUTYL ESTER](/CAS/GIF/723286-79-1.gif)
723286-79-1
723286-80-4
The general procedure for the synthesis of 7-Boc-3-bromo-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine using 7-Boc-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine as a starting material was as follows: 7-Boc-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (1 g ) was dissolved in chloroform (20 mL) and sodium bicarbonate (688 mg) and N-bromosuccinimide (873 mg) were added sequentially at 0 °C in an ice bath. The reaction mixture was stirred at 0 °C for 2 hours. Upon completion of the reaction, the reaction solution was brought back to room temperature and the reaction was quenched by the addition of an appropriate amount of water, followed by three extractions with chloroform. The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography to afford the target compound 7-Boc-3-bromo-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrazine (693 mg, 51% yield). lRMS (ESI) m/z 303 [M+H]+.
723286-79-1
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$41.00/100mg
723286-80-4
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$26.00/100mg
Yield: 51%
Reaction Conditions:
with N-Bromosuccinimide;sodium hydrogencarbonate in chloroform at 0 - 20; for 2 h;
Steps:
3.4 Synthesis of tert-butyl 3-bromo-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-carboxylate
The compound obtained in Step 3 (1 g) was dissolved in chloroform (20 mL), sodium bicarbonate (688 mg) and N- bromosuccinimide (873 mg) was added at 0 ° C., the-reaction solution was stirred for 2 hours at room temperature and extracted 3 times with chloroform after addition of water, the organic layer gave the title compound by the residue obtained, which was concentrated after drying over sodium sulfate and purified by silica gel column chromatography (693mg, 51%). LRMS (ESI) m / z 303 [M + H] +.
References:
TAIHO PHARMACEUTICAL COMPANY LIMITED;MINAMIGUCHI, KAZUHISA;OKAJIMA, SHIGEO;AOKI, SHINICHI;ASAI, MASANORI;ASAI, TAKAHIRO;YAMANAKA, HIROYOSHI;DOHI, SUGURU JP5851663, 2016, B1 Location in patent:Paragraph 0303
![1,2,4]TRIAZOLO[4,3-A]PYRAZINE](/CAS/GIF/274-82-8.gif)
274-82-8
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723286-80-4
131 suppliers
$26.00/100mg
![8-CHLORO-[1,2,4]TRIAZOLO[4,3-A]PYRAZINE](/CAS/GIF/68774-77-6.gif)
68774-77-6
122 suppliers
$16.00/250mg
723286-80-4
131 suppliers
$26.00/100mg