tert-butyl 3-bromo-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazine-5(4H)-carboxylate synthesis

3synthesis methods

Product Name:tert-butyl 3-bromo-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazine-5(4H)-carboxylate
CAS Number:1251002-97-7
Molecular formula:C10H15BrN4O2
Molecular Weight:303.16

6,7-Dihydro-[1,2,3]triazolo[1,5-a]pyrazine-5(4H)-carboxylic acid tert-butyl ester

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tert-butyl 3-bromo-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazine-5(4H)-carboxylate

1251002-97-7
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Yield:1251002-97-7 49%

Reaction Conditions:

with NBS in acetonitrile at 0 - 20;

Steps:

tert-butyl 3-bromo-6,7-dihydro-[1,2,3]triazolo[1,5-a]pyrazine-5(4H)-carboxylate (8a)

To a solution of 7a (13.4 g, 0.06 mol) in CH₃CN (150 mL) was added NBS (12.8 g, 0.072 mol) at 0^oC, and the mixture was stirred overnight at room temperature. The solution was concentrated under reduced pressure and purified by column chromatography (hexanes/EtOAc = 5/1) to obtain 8a (8.9 g, 49%) as a yellow solid. ¹H NMR (CDCl₃, 400 MHz): δ 1.48 (s, 9H), 3.89 (t, J = 5.2 Hz, 2H), 4.38 (t, J = 5.2 Hz, 2H), 4.57 (s, 2H).

References:

Shan, Zhenwei;Peng, Min;Fan, Houxing;Lu, Qingtao;Lu, Peng;Zhao, Chuansheng;Chen, Yilang [Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,# 6,p. 1731 - 1735] Location in patent:supporting information; experimental part

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References

5-benzyl-4H,5H,6H,7H-[1,2,3]triazolo[1,5-a]pyrazine

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References