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General procedure: To a solution of 4-bromopentane-2,3-dione (1.79 g, 10.00 mmol) in ethanol (50 mL) was added thiourea (760 mg, 9.98 mmol). The resulting solution was stirred for 1 h at 100 °C and then cooled down room temperature. The mixture was filtered to afford l-(2-amino-5-methyl-l,3-thiazol-4-yl)ethan-l-one as a off-white solid (1.2 g, 65percent). LCMS (ESI): [M+H]+ = 157.0.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5879 - 5882
[2] Patent: WO2015/52226, 2015, A1, . Location in patent: Paragraph 0353
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2760 - 2779
General procedure: To a solution of 4-bromopentane-2,3-dione (1.79 g, 10.00 mmol) in ethanol (50 mL) was added thiourea (760 mg, 9.98 mmol). The resulting solution was stirred for 1 h at 100 C and then cooled down room temperature. The mixture was filtered to afford l-(2-amino-5-methyl-l,3-thiazol-4-yl)ethan-l-one as a off-white solid (1.2 g, 65%). LCMS (ESI): [M+H]+ = 157.0.
3-acetyl-7-(chloromethyl)-2-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
12%
With polyphosphoric acid; at 110℃; for 1.0h;
To a solution of l-(2-amino-5-methyl-l,3-thiazol-4-yl)ethan-l-one (300 mg, 1.92 mmol) was added ethyl 4-chloro-3-oxobutanoate (474 mg, 2.88 mmol) and polyphosphoric acid (10 mL). The resulting solution was stirred for 1 h at 110 C and then cooled down room temperature. The resulting solution was diluted with water (20 mL) and the pH value of the solution was adjusted to 8. The resulting solution was extracted and concentrated in vacuo. The residue was purified by chromatography with ethyl acetate/petroleum (1/1) to afford 3-acetyl-7-(chloromethyl)-2-methyl-5H-[l,3]thiazolo[3,2- a]pyrimidin-5-one as a light yellow solid (70.0 mg, 12%). LCMS (ESI): [M+H]+ = 257.0; lU NMR (300 MHz, CDC13) delta 6.46 (s, 1H), 4.42 (s, 2H), 2.52 (s, 3H), 2.39 (s, 3H).
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