反应详情

A solution of 4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyrimidine (2-3, 500 mg, 2.323 mmol 1.0 eq.) in toluene (35 mL) was heated under nitrogen to 120° C. To the reaction mixture was added ethyl diazoacetate (0.602 mL, 5.81 mmol, 2.5 eq.) dropwise. Upon complete addition, heating was continued for 2 hours. A mix of trans (major) and cis (minor) products were observed. Toluene was removed by roto-evaporation and the resulting residue purified by silica gel column chromatography (0-100% ethyl acetate in hexanes). The major product peak was collected and concentrated to afford ethyl 2-(6-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl)cyclopropanecarboxylate (2-4). 1H NMR (500 MHz, CDCl3) δ 7.59 (s, 1H), 4.18 (m, 2H), 2.89 (s, 3H), 2.62 (s, 3H), 2.60 (m, 1H), 2.41 (s, 3H), 2.36 (m, 1H), 1.71 (m, 1H), 1.66 (m, 1H), 1.28 (t, 3H, J=6.4 Hz). LRMS m/z (M+H) 302.3 found, 302.2 required.

1. additionUpon complete addition
2. temperatureheating
3. additionA mix of trans (major) and cis (minor) products
4. customToluene was removed by roto-evaporation
5. customthe resulting residue purified by silica gel column chromatography (0-100% ethyl acetate in hexanes)
6. customThe major product peak was collected
7. concentrationconcentrated