6-Bromo-2-methylthiazolo[5,4-b]pyrazine synthesis

4synthesis methods

Product Name:6-Bromo-2-methylthiazolo[5,4-b]pyrazine
CAS Number:87444-41-5
Molecular formula:C6H4BrN3S
Molecular Weight:230.09

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Yield:87444-41-5 74%

Reaction Conditions:

with tetraphosphorus decasulfide in toluene at 110; for 1 h;

Steps:

6-Bromo-2-methylthiazolo[4,5-b]pyrazine (3)

A mixtureof 4 (659.5 mg, 2.25 mmol) and P4S10 (300.3 mg, 0.68 mmol)in toluene (10 mL) was stirred at 110 °C for 1 h. After themixture was cooled to room temperature, precipitates werefiltered. The filtrate was concentrated. The crude mixturewas purified by silica gel column chromatography (hexane/EtOAc = 1/1, Rf 0.5) to afford the title compound as whitesolids (380.7 mg, 74%). Melting point: 135-136 °C; 1H-NMR(CDCl3) δ: 8.71 (s, 1H), 2.93 (s, 3H); 13C-NMR (CDCl3) δ:173.2, 156.7, 152.6, 144.7, 135.8, 22.1; HRMS (ESI+): m/zCalcd for C5H2N3SBrNa+ [M + Na]+ 251.9207. Found 251.9211.

References:

Sawazaki, Taka;Sohma, Youhei;Kanai, Motomu [Chemical and Pharmaceutical Bulletin,2022,vol. 70,# 1,p. 82 - 84]