ChemicalBook CAS DataBase List 8-BROMO-4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE

8-BROMO-4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE synthesis

10synthesis methods

Product Name:8-BROMO-4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE
CAS Number:54346-33-7
Molecular formula:C6H4BrClN4S
Molecular Weight:279.54

8-Bromo-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4-ol

54346-35-9
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$320.00/500mg

8-BROMO-4-CHLORO-2-METHYLTHIOPYRAZOLO[1,5-A]1,3,5-TRIAZINE

54346-33-7
25 suppliers
$410.00/500mg

Yield:54346-33-7 600 mg

Reaction Conditions:

with N,N-dimethyl-aniline;trichlorophosphate at 130; for 4 h;

Steps:

111.5 [00738] Step 5: 8-Bromo-4-chloro-2-methylsulfanylpyrazolo[1,5-a] [1,3,5]triazine

A suspension of 8-bromo-2-methylsulfanyl-3H-pyrazolo[l,5-a][l,3,5]triazin-4-one (2.0 g, 6.13 mmol, 1 eq) and N,N-dimethylaniline (742.58 mg, 6.13 mmol, 776.76 μ_, 1 eq) in POCb (16.50 g, 107.61 mmol, 10 mL, 17.56 eq) was stirred at 130 °C for 4 h. The mixture was added into water (100 mL) at 0 °C, extracted with EtOAc (200 mL x 3). The combined organic layers were washed with brine (50 mL), dried over Na2S04, filtered and concentrated. The crude material was purified on silica gel column chromatography (from pure PE to PE/EtOAc = 3/1, TLC: PE/EtOAc = 3/1, Rf = 0.8) to yield 8-bromo-4-chloro-2-methylsulfanyl-pyrazolo[l,5-a][l,3,5]triazine (600 mg, 2.08 mmol, 33.9% yield, 97% purity) as a white solid. NMR (400 MHz, CDCb) δ ppm 8.12 (s, 1H), 2.66 (s, 3H); ES-LCMS m/z 278.9, 280.9 [M+H]+.

References:

WO2018/195397,2018,A2 Location in patent:Paragraph 00733; 00738

54346-19-9 Synthesis