反応 #744881

反応方程式

mixture

6-ethynyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

methyl 2-(4-bromophenyl)-2-methylpropanoate

triethylamine

→

title compound

収率 45.8%

methyl 2-{4-[(7-amino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)ethynyl]phenyl}-2-methylpropanoate

収率 45.8%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他The resulting mixture was partitioned between ethyl acetate and water
2. 2
   洗浄The organic phase was washed with brine
3. 3
   乾燥dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated in vacuuo
6. 6
   その他The residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate)

実験手順

A mixture of Example 72B (17 mg, 0.1 mmol), methyl 2-(4-bromophenyl)-2-methylpropanoate (38 mg, 0.15 mmol), bis(triphenylphosphine)palladium(II) dichloride (3.5 mg, 0.005 mmol), CuI (1 mg, 0.005 mmol), and triethylamine (28 μL, 0.2 mmol) in acetonitrile (500 μL) was heated at 95° C. under nitrogen for 1 h. The resulting mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuuo. The residue was purified by flash chromatograph on silica gel (eluting with ethyl acetate) to provide the title compound as a white solid (16 mg, 45% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 3H), 7.64 (d, J=8.48 Hz, 2H), 7.36 (d, J=8.48 Hz, 2H), 3.61 (s, 3H), 2.60 (s, 3H), 1.52 (s, 6H). MS (ESI) m/z 350 (M+H)+.

出典