反应详情

温度

105 °C

To a round bottom was added 5-bromo-pyrimidine-2-carboxylic acid methyl ester (14.50 g, 66.81 mmol), (+/−)-BINAP (4.16 g, 6.68 mmol), Pd(OAc)2 (750 mg, 3.34 mmol), and Cs2CO3 (26.1 g, 80.2 mmol). Toluene (100 mL) and benzophenone imine (12.3 mL, 73.5 mmol) were added and the mixture heated to 105° C. as an orange mixture. At 17 h, the reaction was cooled and partitioned between ethyl acetate and 1 N NaOH. The aqueous layer was extracted with ethyl acetate and the combined organics dried over MgSO4. Purification by silica gel flash chromatography (ethyl acetate/heptane) gave 5-(benzhydrylidene-amino)-pyrimidine-2-carboxylic acid methyl ester (9.83 g, 46%) as a bright yellow solid. 1H NMR (400 MHz, DMSO-d6, δ): 8.42 (s, 2H) 7.74 (d, J=6.8 Hz, 2H) 7.61 (m, 1H) 7.54 (m, 2H) 7.38 (br. s., 3H) 7.26 (br. s., 2H) 3.83 (s, 3H); MS (M+1): 318.2.

1. temperaturethe reaction was cooled
2. custompartitioned between ethyl acetate and 1 N NaOH
3. extractionThe aqueous layer was extracted with ethyl acetate
4. dry with materialthe combined organics dried over MgSO4
5. customPurification by silica gel flash chromatography (ethyl acetate/heptane)