反应详情

温度

110 °C

A pressure vessel is charged with 2-cyanopyrimidine (7.88 g, 75 mmol), N-acetyl cysteine (1.22 g, 7.5 mmol), ammonium acetate (6.93 g, 90 mmol), and MeOH (75 mL). The vessel is sealed and heated at 110° C. for 1.5 h, and then cooled to rt. To the reaction mixture is added sodium 2-ethoxycarbonyl-3-oxo-but-1-en-1-olate (17 g, 86.25 mmol) and MeOH (75 mL). The mixture is heated to reflux for 1.5 h and then cooled to rt. NaOH (6 g, 150 mmol) and water (80 mL) are added. The mixture is stirred for 30 min or until LC-MS indicates complete hydrolysis of the intermediate ester. The pH of the reaction mixture is adjusted to 3 with concentrated (12 M) aqueous HCl. MeOH is evaporated in vacuo, and the resulting precipitate is collected via filtration and washed with minimal chilled water to yield [2,2′]bipyrimidinyl-5-carboxylic acid (59%). MS: 203 (M+H); 1H NMR (300 MHz, CDCl3): δ=7.71 (t, 1H), 9.06 (d, 2H), 9.40 (s, 2H).

1. customThe vessel is sealed
2. temperaturecooled to rt
3. temperatureThe mixture is heated
4. temperatureto reflux for 1.5 h
5. temperaturecooled to rt
6. concentrationwith concentrated (12 M) aqueous HCl
7. customMeOH is evaporated in vacuo
8. filtrationthe resulting precipitate is collected via filtration
9. washwashed
10. temperaturewith minimal chilled water