Triethylamine → 5-(5-bromo-1-methyl-1H-pyrazol-4-yl)-4-chloro-7-methylimidazo[5,1-f][1,2,4]triazine

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A mixture of 5-(5-bromo-1-methyl-1H-pyrazol-4-yl)-7-methylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (10.00 g, 32.35 mmol) in toluene (100 mL) was treated with phosphorus oxychloride (9.05 mL, 97.1 mmol). After drop-wise addition of N,N-diisopropylethylamine (28.2 mL, 162 mmol), the mixture was heated at 105° C. for 24 hours. The reaction was allowed to cool to room temperature, and then was diluted with dichloromethane (20 mL) and added over 10 minutes to a solution comprised of triethylamine (30 mL), toluene (50 mL) and water (80 mL), while keeping the internal temperature below 36° C. After an additional 20 minutes of stirring, the phases were separated, and the aqueous layer (pH ˜7) was extracted with toluene (100 mL). The combined organic layers were washed with aqueous citric acid solution (1 M, 150 mL), then washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to provide the product as a solid. Yield: 9.80 g, 29.9 mmol, 92%. LCMS m/z 328.9 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.78 (s, 3H), 3.97 (s, 3H), 7.75 (s, 1H), 8.18 (s, 1H).

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